Novel imidate insecticides

ABSTRACT

A series of novel imidate insecticides distinguished by the general formula ##STR1## in which R 1  is an optionally substituted aryl group in which the substituents are halo, C 1  -C 4  alkyl, C 1  -C 4  haloalkoxy, C 1  -C 4  alkoxy, C 1  -C 4  haloalkylthio, C 3  -C 6  cycloalkyl, nitro, C 1  -C 4  haloalkyl, C 2  -C 5  carboalkoxy, C 1  -C 4  alkylthio, cyano, C 1  -C 4  alkylsulfonyl, C 2  -C 4  haloalkylsulfonyl; C 2  -C 5  alkylcarbonyl, C 2  -C 4  alkyleneoxy, C 1  -C 2  perhaloalkyleneoxy; C 1  -C 4  alkylendioxy, C 1  -C 3  halo-substituted alkylenedioxy, phenyl, mono-substituted phenyl, pyridyloxy, C 2  -C 4  alkylene, C 2  -C 4  alkenyl, C 3  -haloalkenoxy; and/or amido; 
     R 2  is C 1  -C 7  alkyl, C 1  -C 6  haloalkyl, cyclopropyl, cyclobutyl, mono- or poly- halo- or methyl-substituted cyclopropyl, cyano, C 2  -C 4  alkoxyalkyl, C 2  -C 6  haloalkenyl or C 2  -C 6  alkenyl; and 
     R 3  is (a) an optionally substituted 3-phenoxyphenalkyl, 3-phenoxypyridylalkyl, 3-(pyridyloxy)phenalkyl, 3-phenylaminophenalkyl, 3-benzylphenalkyl or benzyloxyphenalkyl moiety; (b) a benzylfuranylmethyl moiety; (c) a 3- or 4-substituted benzyl or tetrafluorobenzyl moiety; (d) 4-phenoxy-2-butyn-2-yl; (e) 2-methyl-3-phenylbenzyl, or (f) 4-(4-trifluoromethyl-2-pyridyloxy)benzyl.

CROSS-REFERENCE TO RELATED APPLICATIONS

This is a continuation-in-part of Application Ser. No. 263,605, filedOct. 31, 1988, and of Application Ser. No. 264,746, filed Oct. 31, 1988,both of which are continuations-in-part of Application Ser. No. 122,877,filed Nov. 17, 1987 all now abandoned.

This invention relates to a series of novel imidate insecticidesdistinguished by the general formula ##STR2## in which R₁ is anoptionally substituted aryl group in which the substituents are halo, C₁-C₄ alkyl, C₁ -C₄ haloalkoxy, C₁ -C₄ alkoxy, C₁ -C₄ haloalkylthio, C₃-C₆ cycloalkyl, nitro, C₁ -C₄ haloalkyl, C₂ -C₅ carboalkoxy, C₁ -C₄alkylthio, cyano, C₁ -C₄ alkylsulfonyl, C₁ -C₄ haloalkylsulfonyl, C₂ -C₅alkylcarbonyl, C₂ -C₄ alkyleneoxy, C₁ -C₂ perhaloalkyleneoxy, C₁ -C₄alkylenedioxy, C₁ -C₃ halo-substituted alkylenedioxy, phenyl,mono-substituted phenyl, pyridyloxy, C₂ -C₄ alkylene, C₂ -C₄ alkenyl, C₃-haloalkenoxy, and/or amido;

R₂ is C₁ -C₇ alkyl, C₁ -C₆ haloalkyl, cyclopropyl, cyclobutyl, mono- orpoly- halo- or methyl-substituted cyclopropyl, cyano, C₂ -C₄alkoxyalkyl, C₂ -C₆ haloalkenyl or C₂ -C₆ alkenyl; and

R₃ is (a) an optionally substituted 3-phenoxyphenalkyl,3-phenoxypyridylalkyl, 3-(pyridyloxy)phenalkyl, 3-phenylaminophenalkyl,3-benzylphenalkyl or benzyloxyphenalkyl moiety; (b) abenzylfuranylmethyl moiety; (c) a 3- or 4-substituted benzyl ortetrafluorobenzyl moiety; (d) 4-phenoxy-2-butyn-2-yl; (e)2-methyl-3-phenylbenzyl; or (f)4-(4-trifluoromethyl-2-pyridyloxy)benzyl.

Compounds of this invention demonstrate activity in controlling varioustypes of insects, including lepidoptera, hemiptera and coleoptera,particularly in foliar application.

Another aspect of this invention involves insecticidal compositionscomprising an insecticidally effective amount of a compound of theinvention with an insecticidally suitable diluent or carrier.

In another aspect, this invention involves a method for controllinginsects by administration of an insecticidally effective amount of acompound or composition of this invention to a locus where control isdesired.

The term "insects" as used herein refers to the broad and commonlyunderstood usage rather than to those creatures which in the strictbiological sense are classified as insects. In addition to thosebelonging to the class Insecta, this term includes some classes ofacarids such as mites and the like.

More particularly, the compounds of formula (I) are those in which:

R₁ is naphthyl, optionally substituted by up to 2 halogens; or phenyl,optionally substituted by one or more of the following: C₂ -C₅carboalkoxy, C₁ -C₄ alkylsulfonyl, C₁ -C₄ haloalkylsulfonyl, C₂ -C₅alkylcarbonyl, C₂ -C₄ alkenyl, C₃ -haloalkenoxy, C₁ -C₄ haloalkylthio,C₃ -C₆ cycloalkyl, phenyl, monosubstituted phenyl, pyridyloxy, C₂ -C₄alkyleneoxy, C₁ -C₂ perhaloalkyleneoxy, C₁ -C₄ alkylenedioxy, C₁ -C₃haloalkylenedioxy, C₂ -C₄ alkylene, amido, nitro, cyano, up to two C₁-C₄ alkylthio groups, up to three C₁ -C₄ alkoxy groups, up to three C₁-C₄ haloalkoxy groups, up to three C₁ -C₄ alkyl groups, up to three C₁-C₄ haloalkyl groups, or up to five halogens;

R₂ is methyl; ethyl; n-propyl; C₃ -C₇ branched alkyl; C₁ -C₆ haloalkyl,cyclopropyl optionally substituted by up to 4 methyl groups or up to 2halogens, cyclobutyl, cyano, C₂ -C₄ alkoxyalkyl, C₂ -C₆ alkenyl or C₂-C₆ haloalkenyl; and

R₃ is

(a) ##STR3## in which m is 0 or 1; A, B and C are each carbon ornitrogen, provided that A, B and C are not all nitrogen and if two of A,B and C are nitrogen, then A and C are nitrogen;

R₄ is hydrogen, monohalo or dihalo;

R₆ is hydrogen, methyl, fluoro or ethynyl; and

R₇ is

(i) ##STR4## in which D and E are each carbon or nitrogen provided thatboth D and E are not nitrogen, and further provided that if any of A, Bor C is nitrogen, then D and E are both carbon; and

R₅ is hydrogen, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, trifluoromethyl, cyano, C₁-C₄ alkylthio, C₁ -C₄ alkylsulfonyl, or mono- or polyhalo;

(ii) ##STR5## in which R₈ is hydrogen or halogen; or (iii) --O--CH₂--CH═CH₂ ;

(b) ##STR6## in which (i) R₉ is 4-fluoro, 4-methoxymethyl, or4-propargyl, and R₁₀ is fluoro or

(ii) R₉ is 3- or 4-allyl, 3- or 4-propargyl, or 3- or 4-(mono- ordihalo)allyl, and R₁₀ is hydrogen or fluoro;

(c) ##STR7## (d) 4-phenoxy-2-butyn-2-yl; (e) 3-bromo-4-fluorobenzyl;

(f) 4-(benzyloxy)benzyl;

(g) 4-(4-fluorobenzyloxy)benzyl;

(h) 4-(4-trifluromethyl-2-pyridyloxy)benzyl; or

(j) ##STR8## provided that: (i) R₁ is not 2,3-dichlorophenyl,2,6-difluorophenyl, 2,6-di(C1-C4 alkyl)phenyl, 2,4,6-tribromophenyl or2,4,6-tri(C₁ -C₄ alkoxy)phenyl;

(ii) when R₂ is tertiary butyl, R₁ is not phenyl, 3-methyl-phenyl,4-(n-butyl)phenyl or 4-(t-butyl)phenyl; and

(iii) when R₂ is a C₅ alkyl group, then R₁ is not 4-isopropylphenyl.

A more preferred class of compounds are those in which R₁ does notcontain substituents at both ortho positions on the phenyl ring, i.e.,in which R₁ does not contain a 2,6-disubstitution,2,3,6-trisubstitution, or a 2,4,6-trisubstitution on the phenyl ring.

An even more preferred class is that in which the phenyl ring of R₁ issubstituted at the 3-, 4-, and/or 5-positions, including mono-, di- andtri-substituted phenyl compounds, as well as phenyl compounds having a3,4-alkylene, alkeneoxy, perhaloalkyeneoxy, alkylenedioxy, orhaloalkylenedioxy substitution. Such compounds more particularly havethe formula ##STR9## in which R₂ and R₃ are as defined above; R₁₁ ishydrogen, halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄alkylthio, C₁ -C₄ haloalkoxy, C₁ -C₄ haloalkylthio, C₂ -C₅ carboalkoxy,C₂ -C₅ alkylcarbonyl, nitro or cyano; R₁₂ is hydrogen, halogen, C₁ -C₄alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄alkylthio, C₁ -C₄ haloalkylthio, C₃ -haloalkenoxy, nitro, cyano, C₂ -C₅alkylcarbonyl, C₁ -C₄ alkylsulfonyl or C₂ -C₅ carboalkoxy; and R₁₃ ishydrogen, halogen, C₁ -C₄ haloalkyl or C₁ -C₄ alkoxy, or R₁₁ and R₁₂taken together are C₂ -C₄ alkylene, C₂ -C₄ alkyleneoxy, C₁ -C₂perhaloalkenenoxy, C₁ -C₄ alkylenedioxy or halo-C₁ -C₃ alkylenedioxy;and R¹⁴ is hydrogen or fluoro; provided that R₁₁, R₁₂ and R₁₃ are notall hydrogens.

One especially preferred subclass of such compounds are those in whichR₁₁ is as defined above, and most preferably is halogen, C₁ -C₄ alkyl,C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy; R₁₂ is a C₁ -C₂polyhaloalkoxy group containing at least one fluorine atom; and R₁₃ ishydrogen or halogen. Examples of such polyhaloalkoxy groups aredifluoromethoxy, trifluoromethoxy, difluorochloromethoxy,difluorobromomethoxy, and 1,1,2,2-tetrafluoroethoxy. In one such type ofcompound, R₁₁ is chloro, R₁₂ is trifluoromethoxy and R₁₃ is hydrogen.

Still another preferred class of compounds is that in which R₁ is 3- or4-trifluoromethylphenyl and R₃ is 2,3,5,6-tetrafluoro-4-propargylbenzyl.

Also of interest are compounds having a 2,5-, 2,3,4- or2,4,5-substitution pattern.

As used herein, these terms have the following meanings:

"Alkyleneoxy" and "alkylenedioxy" refer to linking groups having 1 or 2oxygen atoms, respectively, and at least one carbon atom (optionallysubstituted) in a chain. The alkyleneoxy moieties have 1-4, preferably2-4, carbon atoms in this chain and include, for instance, ethyleneoxy(--O--C₂ H₄ --), dihalomethyleneoxy, dihaloethyleneoxy, and the like.Alkylenedioxy moieties include methylenedioxy (--O--CH₂ --O--),1,2-ethylenedioxy (--O--C₂ H₄ --O--), mono- or di-halomethylenedioxy (amethylenedioxy group in which one or both hydrogens are replaced by ahalogen) and isopropylenedioxy (--O--C(CH₃)₂ --O--).

The term "carboalkoxy" refers to a group having the formula ##STR10## inwhich R₁₅ is an alkyl group. The carbon atom content of the carboalkoxygroup is meant to include the carbon atom of the carbonyl moiety in thatgroup. Thus, C₂ -carboalkoxy refers to carbomethoxy, etc. Similarly, thecarbon atom content of an alkylcarbonyl group includes the carbon atomin the carbonyl moiety. The simplest member of this group is thusacetyl, CH₃ C(O)--.

When R₁ represents a phenyl ring substituted by a second phenyl ring,the second phenyl ring may be unsubstituted or mono-substituted in whichthe substituent is halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, nitro,cyano, C₁ -C₄ alkylsulfonyl, C₁ -C₄ haloalkylsulfonyl, or C₁ -C₄alkylenedioxy (optionally further substituted by up to 2 halogens).

Terms defining halogenated groups such as "haloalkyl", "haloalkoxy","haloalkenyl", "haloalkenoxy" and the like include mono- andpolyhalogenated groups of the indicated number of carbon atoms. Inpolyhalogenated groups the halogens may be the same or different.

"Propargyl" refers to the 2-propynyl group --CH₂ --C═CH and "allyl"refers to the 2-propenyl group --CH₂ --CH═CH₂.

Cyclopropyl groups for R₂ may be substituted by up to 4 methyl groups oralternatively up to 2 halogen atoms.

For the various subgroups falling within the general definition of R₃,preferred types are:

For R₄ : hydrogen and 2-, 4- or 6-monohalo, particularly monochloro ormonofluoro;

For R₅ : 2-, 3- or 4-halo, 2,4-, 3,4- or 3,5-dihalo, particularlydifluoro, pentahalo, particularly pentafluoro, 4-methyl,4-trifluoromethyl, 4-methoxy, 4-methylthio and 4-methylsulfonyl.

The following are examples of specific embodiments of groups fallingwithin the definition of R₃. For convenience in specifying positions ofsubstitution of compounds of the type ##STR11## the position ofattachment of the group ##STR12## was given the number 1 and theposition of attachment of group R₇, the number 3. When A, B or C was anitrogen atom, the compounds were designated pyrid-2-yl, pyrid-6-yl orpyrid-4-yl, respectively.

3-phenoxybenzyl,

3-phenoxy-(alpha-methyl)benzyl,

3-phenoxyphenethyl,

3-(4-pyridyloxy)benzyl,

3-(4-fluorophenoxy)benzyl,

3-(4-chlorophenoxy)benzyl,

3-(4-bromophenoxy)benzyl,

3-(4-iodophenoxy)benzyl,

3-(2,4-difluorophenoxy)benzyl,

3-(3,4-difluorophenoxy)benzyl,

3-(3,5-difluorophenoxy)benzyl,

3-(2,3,4,5,6-pentafluorophenoxy)benzyl,

3-(4-fluorophenoxy)-4-fluorobenzyl,

3-(4-fluorophenoxy)-4-chlorobenzyl,

3-(4-chlorophenoxy)-4-fluorobenzyl,

3-phenoxy-4-fluorobenzyl,

3-(4-fluorophenoxy)-6-chlorobenzyl,

3-(4-fluorophenoxy)-5-fluorobenzyl,

3-(4-fluorophenoxy)-4,6-difluorobenzyl,

3-(4-fluorophenoxy)-6-fluorobenzyl,

3-(4-fluorophenoxy)-2-fluorobenzyl,

3-(4-cyanophenoxy)benzyl,

3-(4-methylphenoxy)benzyl,

3-(4-methoxyphenoxy)benzyl,

3-(3,4-difluorophenoxy)-4-fluorobenzyl,

3-(3-fluorophenoxy)benzyl,

3-(2-fluorophenoxy)benzyl,

3-(3-chlorophenoxy)benzyl,

3-(4-trifluoromethylphenoxy)benzyl,

3-(4-methylthiophenoxy)benzyl,

3-(4-fluorophenoxy)-(alpha-fluoro)benzyl,

3-phenoxy-pyrid-2-yl-methyl,

3-phenoxy-pyrid-4-yl-methyl,

3-phenoxy-pyrid-6-yl-methyl,

3-(4-fluorophenoxy)pyrid-2-ylmethyl,

3-(4-chlorophenoxy)pyrid-2-ylmethyl,

3-(4-fluorophenoxy)pyrid-4-ylmethyl,

3-(4-chlorophenoxy)pyrid-2-ylmethyl,

3-(4-chlorophenoxy)pyrid-4-ylmethyl,

3-(4-chlorophenoxy)pyrid-6-ylmethyl,

3-(3,4-difluorophenoxy)pyrid-2-ylmethyl,

3-(4-methylphenoxy)pyrid-2-ylmethyl,

3-(4-fluorophenoxy)pyrid-6-ylmethyl,

3-(pyrid-2-yloxy)benzyl,

3-(4-chloropyrid-2-yloxy)benzyl,

2,3,4,5,6-tetrafluorobenzyl,

4-methoxymethyl-2,3,5,6-tetrafluorobenzyl,

4-propargyl-2,3,5,6-tetrafluorobenzyl,

3-allyloxybenzyl,

3-(benzyl)benzyl,

3-(benzyloxy)benzyl,

3-(4-fluorobenzyloxy)benzyl,

3-(phenylamino)benzyl,

3-(4-fluorophenylamino)benzyl,

1-(3-phenoxyphenyl)prop-2-ynyl,

3-bromo-4-fluorobenzyl,

4-phenoxy-2-butyn-2-yl,

4-(benzyloxy)benzyl,

4-(4-fluorobenzyloxy)benzyl,

4-(4-trifluoromethyl-2-pyridyloxy)benzyl

2-methyl-3-phenylbenzyl,

5-benzyl-3-furanylmethyl.

PROCESSES FOR PREPARATION OF COMPOUNDS OF THIS INVENTION Process (A)

Compounds of this invention in general are prepared by reaction of animidoyl halide (preferably chloride) with an alkali metal alkoxideaccording to the general reaction: ##STR13## in which M is an alkalimetal, preferably sodium or potassium and Hal is a halogen, particularlychloro or bromo.

This reaction is conducted at a temperature of from about -70° C. toabout +65° C., most preferably at about room temperature, for a timewhich may range from about 5 minutes to about 24 hours. The reaction isconducted in the presence of a solvent, for example, an aromatichydrocarbon such as benzene, toluene, or xylene or an ether, such asdiethyl ether, diisopropyl ether, diisoamyl ether, dibutyl ether, furan,1,2-dimethoxyethane, or tetrahydrofuran (preferably tetrahydrofuran). Insome instances, apparent to those skilled in the art, it is advantageousto add the solution of the alkali metal alkoxide to a solution of theimidoyl halide or to use substantial excesses of alkoxide. The resultingproduct may be recovered by conventional techniques.

The alkoxide R₃ OM is produced by reaction of an appropriate alcohol,such as 3-phenoxybenzyl alcohol, with an alkali metal-containing base,for instance, an alkali metal hydride (e.g., potassium or preferablysodium hydride) in the presence of a solvent such as that used inreaction of the alkali metal alkoxide with the imidoyl halide. Ingeneral, this reaction is conducted at reflux temperature under an inertatmosphere for a time which may range up to about 2 hours.

The alcohols, if not commercially available, can be prepared accordingto known methods such as those described in the following references:U.S. Pat. Nos. 4,256,893; 4,261,920; and 4,329,518, and Volume 7 of thetext "Chemie der Pflanzenschutz und Schadlingsbekampfungsmittel"(phenoxybenzyl, phenoxypyridylmethyl and pyridyloxy type alcohols);Elliott et al, J. Chem Soc. (C), 1971, pp. 2551-1554(5-benzyl-2-furanylmethanol); Pesticide Science 14, 560-570 (1983)(2-methyl-3-phenylbenzyl alcohol); U.S. Pat. Nos. 4,370,346 and4,594,355; British patent 2,122,616; European patent applications196,156 and 271,240; and J. Sci. Food & Agriculture 18, 167 (1967) forvarious substituted benzyl alcohols; European patent application 211,561for 3-phenylaminobenzyl alcohols; Swiss patent 549,342 for4-phenoxy-2-butyn-1-ol; and Japanese patent 49-27331 for1-(3-phenoxyphenyl)-2-propyn-1-ol.

The imidoyl halide may be prepared from a starting amine having theformula R₁ NH₂ or amide having the formula ##STR14## depending onavailability. The amines are either generally available or may beprepared by procedures known in the art, for example, those described in"Compendium of Organic Synthetic Methods", Harrison et al.(Wiley-Interscience, New York, 1971).

The amides, if not available, may be produced by reaction of the aminewith an appropriate acid chloride having the formula ##STR15## Thetemperature of this reaction ranges from about -40° C. to about +80° C.Suitable solvents include hydrocarbon solvents such as toluene andchlorinated hydrocarbon solvents such as methylene chloride, chloroform,carbon tetrachloride, ethylene dichloride, tetrachloroethane and thelike, preferably methylene chloride. This reaction is conducted in thepresence of a base, preferably a tertiary amine. Suitable bases includetriethylamine, quinoline, dimethylaniline, diethylaniline, and pyridine.Triethylamine is the preferred base. The resulting amide is recoveredand purified by conventional means.

The imidoyl halide may be prepared from the amide by reacting it with ahalogenating agent such as phosphorus pentachloride or phosgene in anorganic solvent such as that utilized in the amide production(preferably methylene chloride) or alternatively using phosphorusoxychloride as the solvent. The reaction is carried out under an inertatmosphere for a time which may be up to 24 hours, preferably from 1 to24 hours, at a temperature of from about 0° C. to about 110° C. Beforethe imidoyl chloride-containing product is passed to the final step, allsubstances, such as phosphorus oxychloride or hydrogen chloride, whichcan react with the alkoxide in the final step, should be removed. Thiscan generally be accomplished by evaporation or distillation.

Alternatively, the compounds of this invention may be prepared by atwo-step process indicated as follows:

Process (B) ##STR16## in which "HX" represents a mineral acid.

In the first step, the appropriate alcohol (for instance a phenoxybenzylalcohol) is mixed with a nitrile having the formula R₂ CN at atemperature of from about -20° C. to about +40° C. Then, a solution of amineral acid such as hydrochloric, hydrobromic, sulfuric or phosphoricacid (preferably hydrochloric acid) dissolved in a suitable organicsolvent is added at temperatures from about -5° to about 40° C.,preferably 0° C., then stirred at room temperature, to produce thecorresponding imidate salt. Suitable solvents for this reaction includearomatic hydrocarbons such as benzene, toluene, or xylene and etherssuch as diethyl ether, diisopropyl ether, diamyl ether, furan,tetrahydrofuran and dioxane (preferably dioxane). Time for the reactionmay be up to 52 hours. The imidate salts are novel and constitute anaspect of this invention.

In the second step, the imidate salt is suspended in an organic solventsuch as that utilized in the previous step, preferably benzene, andreacted with an amine having the formula R₁ NH₂. The mixture is reacted,optionally with stirring, at a temperature of between about -50° and+80° C., most preferably at room temperature, for a period of timenecessary to conduct the reaction, which may be up to 120 hours. Thefinal imidate product may be recovered as in process (A).

Process (C)

A third process may be used for producing many of the compounds of thisinvention, with the exception of those in which R₂ is a group having noalpha-hydrogen, such as cyano, tertiary butyl, vinyl or halovinyl. Thisprocess proceeds by way of an intermediate ketenimine, which may beprepared from the amide or from the imidoyl halide. In the first case,the amide (prepared for instance, as described in process A) is reactedwith an inexpensive base and a trivalent phosphorus compound, preferablytriphenylphosphine. The base is preferably a tertiary amine such astriethylamine. The reaction is carried out at a temperature of fromabout -10° C. to 40° C. in the presence of a halogen, preferablychlorine or bromine, and an aromatic or chlorinated hydrocarbon solventsuch as benzene, toluene, xylene, methylene chloride, ethylenedichloride, chloroform, carbon tetrachloride, tetrachloroethane and thelike, preferably methylene chloride. The reaction may then be conductedunder reflux temperature of the solvent and the ketenimine recoveredaccording to methods known in the art.

Alternatively, the ketenimine may be prepared by reaction of the imidoylhalide with a base, as just described, but no halogen or trivalentphosphorus compound present.

In the second step of this process, the ketenimine is reacted with analcohol having the formula R₃ OH in the presence of a solvent,preferably an ether solvent, such as diethyl ether, dipropyl ether,diisopropyl ether, dibutyl ether, tetrahydrofuran or 1,2-dimethoxyethaneand an alkali metal base such as potassium or sodium hydride, preferablysodium hydride. This reaction is conducted under reflux for a time asnecessary which may be up to 48 hours, preferably from about 2 to about10 hours, at the end of which the reaction mixture is cooled and theimidate product recovered as described above.

This process can be depicted by the general scheme: ##STR17## in whichR₁, R₂ and R₃ are as previously described and R₁₆ and R₁₇ areindependently hydrogen, C₁ -C₆ alkyl, halo, C₁ -C₅ haloalkyl, C₁ -C₃alkoxy, C₂ -C₅ alkenyl or C₂ -C₅ haloalkenyl, or R₁₇ and R₁₈ takentogether are a C₂ -C₃ alkylene chain optionally substituted by up to 4methyl groups or up to 2 halogens.

Ketenimines ##STR18## are novel.

Process (D)

This process may be used as an alternative to process (A) forpreparation of compounds of this invention from alcohols (R₃ OH) whichare sensitive to, and could be adversely affected (e.g. decomposed) by,strong bases such as the alkali metal-containing bases (e.g. alkalimetal hydrides) used to prepare the alkoxides (R₃ OM). Alcohols whichmay be sensitive to such strong bases include phenoxypyridyl alkanols,alpha-ethynyl alcohols (R₆ is ethynyl) such as1-(3-phenoxyphenyl)-2-propyn-1-ol and tetrafluoropropargylbenzylalcohol.

Compounds of this type may be made by direct reaction of the alcoholwith the imidoyl chloride in the presence of a tertiary amine base and areaction-promoting amount of a 4-di(lower alkyl)aminopyridine,preferably 4-dimethylaminopyridine.

Tertiary amines which may be used in this process include trialkylaminessuch as trimethyl-, triethyl-, tri-n-butylamine and the like, includingtertiary amines having mixed alkyl groups, N,N-dialkylanilines such asN,N-dimethylaniline, pyridine and various substituted pyridines.

Preferred tertiary amines, primarily for economic reasons, aretriethylamine, N,N-dimethylaniline, and pyridine. The tertiary amine mayeven be an additional amount of the promoter 4-di(loweralkyl)aminopyridine, over and above that amount needed for promoting thereaction.

The tertiary amine is preferably used in a stoichiometric amount withrespect to the alcohol, but may be used in excess of that amount. Thepromoter 4-di(lower alkyl)aminopyridine may be used in an amount fromabout 0.05 to about 1 equivalent per equivalent of alcohol, preferablyfrom about 0.05 to about 0.15 equivalent per equivalent, most preferablyabout 0.1.

This process is preferably conducted at temperatures of from about 10°C. to about 50° C. Lower temperatures may be used, but the reaction ratewould be much slower. The process is carried out in the presence of aninert solvent such as an aromatic hydrocarbon (for instance, benzene,toluene or xylene), a chlorinated solvent (such as methylene chloride,ethylene dichloride or chlorobenzene) or an ether (such as diethylether, dioxane or tetrahydrofuran).

While this process is particularly suitable for producing compounds frombase-sensitive alcohols, it may be used to produce compounds of thisinvention in general from other alcohols as described.

Alpha-fluorophenoxybenzyl compounds are made from the alpha-fluorobenzylhalide (preferably bromide) rather than the alcohol by reaction with anamide, R₁ NHCOR₂, in the presence of a halide ion binding agent such assilver oxide or a silver salt, and an inert solvent. Reactiontemperatures are from about -20° C. to about 100° C.

The following are representative examples of the preparation ofcompounds of this invention according to the processes described above.

EXAMPLE 1 Preparation ofN-(3-Chloro-4-fluorophenyl)-O-(3-phenoxybenzyl)isobutyrylimidate(Compound 88 herein) (Process A)

(a) Preparation of the Anilide

To a stirred solution of 3-chloro-4-fluoroaniline (10.0 g, 0.069 mol)and triethylamine (11.2 ml, 0.08 mol) in 100 ml methylene chloride wasadded isobutyryl chloride (7.8 ml, 0.075 mol) dropwise, with cooling, inan ice bath. After the addition, the reaction mixture was permitted toreach room temperature at which point 100 ml of water was added. Theaqueous and organic layers were separated; the organic layer was driedover anhydrous sodium sulfate and the solvent evaporated to provide 15.2g (103% of theoretical yield) of a tan solid, spectroscopicallyidentified as 3-chloro-4-fluoroisobutyrylanilide, m.p. 114°-117° C.

(b) Preparation of the Imidoyl Chloride

To a solution of the anilide prepared in step (a) (2.1 g, 9.3 mmol) in50 ml methylene chloride under an argon atmosphere there was addedphosphorus pentachloride (1.93 g, 9.3 mmol). After two hours, thesolvent was evaporated at 20 mmHg and the resulting brown oil wasfurther evaporated at 40° C. and less than 1 mmHg. The product,N-(1-chloro-2-methylpropylidene)-3-chloro-4-fluoroaniline, wastransferred to the next step without further purification.

(c) Preparation of the Sodium Alkoxide

A suspension of sodium hydride (0.26 g, 11 mmol) in tetrahydrofuran (40ml) was prepared and stirred under an argon atmosphere. To thissuspension there was added 3-phenoxybenzyl alcohol (1.75 ml, 10 mmol).The resulting mixture was heated to reflux 0.5 hour and then cooled.There was obtained a pale yellow solution of sodium3-phenoxybenzylalkoxide which contained a small amount of gray solid.

(d) Preparation of the Imidate

To the alkoxide solution produced in step (c) there was added theimidoyl chloride prepared in step (b), dissolved in about 10 mltetrahydrofuran, at room temperature with cooling over several minutes.At the end of one hour, the product mixture was poured into about 200 mlhexanes and filtered through a pad of silica gel. The solvent wasevaporated to produce 3.0 g (82% of theoretical yield) of a tan oil,which was further purified by chromatography over silica gel.Evaporation of the solvent from the product fraction gave 2.4 g (65% oftheoretical yield) of a nearly colorless, viscous oil, identifiedspectroscopically as the desired product.

EXAMPLE 2 (Process B)

This example illustrates the preparation of the compound of Example 1 bythe second described process, through the intermediate imidate salt.

(a) A solution of 3-phenoxybenzyl alcohol (10 ml, 57.4 mmol) andisobutyronitrile (5.2 ml, 57.88 mmol) was cooled to 0° C. There was thenadded 12.5 ml of a 4.1 molar solution of anhydrous HCl (62.5 mmol) indioxane, dropwise, followed by stirring at 25° C. for 16 hours. Theproduct, O-(3-phenoxybenzyl)isobutyrylimidate hydrochloride, separatedout as a white solid.

(b) The imidate hydrochloride salt obtained above (0.99 g, 3.2 mmol) wassuspended in 15 ml benzene and 0.60 g (4.1 mmol)3-chloro-4-fluoroaniline was added. The mixture was then stirred at 25°C. for 72 hours and filtered through silica gel. The combined filtrateswere concentrated at reduced pressure and purified on silica gel using5% ethylacetate in hexanes as eluent. There was obtained 0.78 g of thedesired product of 77% purity.

EXAMPLE 3 Preparation ofN-(3,4-Difluorophenyl)-O-(4'-fluoro-3-phenoxybenzyl)isobutyrylimidate(Compound 66 herein) (Process C)

This example illustrates production of a compound of this inventionaccording to the third process, through an intermediate ketenimine.

(a) A mixture was prepared which contained 3,4-difluoroisobutyrylanilide(4.0 g, 20.1 mmol, prepared analogously to Example 1, step (a)),triethylamine (6 ml, 43 mmol) and triphenylphosphine (5.3 g, 20.2 mmol)and 50 ml methylene chloride. The mixture was cooled to 0° C.; thenbromine (1.0 ml, 20 mmol) was added dropwise. The mixture was thenrefluxed for 2 hours, cooled to room temperature and concentrated atreduced pressure. The residue was extracted with 50 ml hexanes; theextract was filtered and concentrated at reduced pressure to yield 3.84g of the crude ketenimine.

(b) The ketenimine thus prepared was combined with3-(4-fluorophenoxy)benzyl alcohol (obtained, for instance, by the methodof Fuchs et al., U.S. Pat. No. 4,242,357) (0.80 g, 3.7 mmol) and theresulting mixture dissolved in 50 ml 1,2-dimethoxyethane. Sodium hydride(0.10 g, 4.2 mmol) was added and the mixture heated at reflux for 2hours. The resulting mixture was allowed to cool, filtered, andconcentrated. The crude product was purified by chromatography on silicagel using 5% ethyl acetate in hexanes as eluent. There was obtained 1.05g (72% of theoretical yield) of the desired product.

EXAMPLE 4 Preparation ofN-(4-Chlorophenyl)-O-(3-phenoxybenzyl)cyclopropylcarboximidate (Compound35 herein) (Process A)

N-(4-chlorophenyl)cyclopropane carboxamide (4.0 g, 20.4 mmol), preparedfrom 4-chloroaniline and cyclopropane carboxylic acid chlorideanalogously to Example 1, step (a)) was dissolved in 50 ml methylenechloride and treated with PCl₅ (4.25 g, 20.4 mmol) all at once, under anargon atmosphere. After 20 minutes, n-pentane was added and the solidwas filtered. The solvents were evaporated at 50° C. yielding a residuallight brown oil, the desired imidoyl chloride. This was taken up in asmall amount of dry tetrahydrofuran.

The imidoyl chloride thus prepared was then added to a solution ofsodium 3-phenoxybenzyl alkoxide prepared using 4.1 g of 3-phenoxybenzylalcohol and 0.5 g of sodium hydride as in Example 1, step (c). Themixture was let stand for 4 hours at room temperature then brieflyheated to reflux and cooled. Water and hexanes were added and theaqueous and organic phases separated. The organic layer was washed withwater, dried over magnesium sulfate and evaporated. The residue wasredissolved in hexanes and filtered through silica gel. Evaporation gavea colorless oil, identified spectroscopically as the desired product.

EXAMPLE 5 Preparation ofN-(3-Trifluoromethylphenyl)-O-(3-phenoxybenzyl)dichloroacetimidate(Compound 72 herein) (Process A)

In a flask were combined 4.2 g (20.2 mol) phosphorus pentachloride,3-trifluoromethyldichloroacetanilide [5.4 g, 19.8 mole, preparedanalogously to Example 1, step (a)] and phosphorus oxychloride (solvent)under argon. The mixture was heated to 60° C. for several hours; thenhexanes were added and the resulting solution filtered. The filtrate wasevaporated and the product imidoyl chloride, an oil, was taken up in asmall amount of dry tetrahydrofuran.

The imidoyl chloride thus prepared was added to a solution of sodium3-phenoxybenzyl alkoxide (prepared analogously to Example 1 step (c)from 4.0 g 3-phenoxybenzyl alcohol and 0.5 g sodium hydride).

The resulting mixture was stirred overnight at ambient temperature; thenwater and hexanes were added, the mixture was phase separated, washedwith 5% HCl and saturated sodium bicarbonate solution, dried overmagnesium sulfate and evaporated to produce an oil. This oil was thenpurified by chromatography over silica gel to give a pale yellow oil,identified spectroscopically as the desired product.

EXAMPLE 6 Preparation ofN-(3,4-Methylenedioxyphenyl)-O-(3-phenoxybenzyl)propionimidate (Compound189 herein) (Process A)

This compound was prepared analogously to Example 1 from 2.0 g (10.4mmol) 3,4-methylenedioxypropionanilide (itself prepared from3,4-methylenedioxyaniline and propionyl chloride), 2.26 g3-phenoxybenzyl alcohol and 0.29 g sodium hydride. There was obtained1.9 g (50% of theoretical yield) of a colorless viscous oil, identifiedspectroscopically as the desired product.

EXAMPLE 7 Preparation ofN-(3-chloro-4-fluorophenyl)-O-[1-(3-phenoxyphenyl)-2-propyn-1-yl]isobutyrimidate(Compound 533 herein) (Process D)

(a) Preparation of the alcohol

A solution was prepared containing 2.4 g (24 mmol)trimethylsilylacetylene in 50 ml tetrahydrofuran. The temperature waskept at -78° C. with stirring. Then 10.0 ml of a 2.5M solution ofn-butyllithium in hexanes was slowly added. After further stirring for15 minutes, 3.5 ml (4.0 g, 20 mmol) 3-phenoxybenzaldehyde was added. Thesolution was stirred at -78° C. for 10 minutes and was allowed to warmto room temperature over 30 minutes.

The reaction was quenched with 5% sodium bicarbonate. Thetetrahydrofuran was removed in vacuo, the aqueous phase was extractedwith methylene chloride and the organic layers combined and dried toproduce a light oil.

A solution of the light oil in methanol was stirred with potassiumcarbonate, then concentrated, dissolved in water and extracted withether. The desired alcohol, 1-(3-phenoxyphenyl)-2-propyn-1-ol (4.3 g,96% of theoretical yield), a light yellow oil, was obtained from theether extracts.

(b) Preparation of the imidate

To a solution of 0.7 g (3.0 mmol) of N-3-chloro-4-fluorophenylisobutyrimidoyl chloride [prepared as in Example 1 (a)-(b)] was addedtriethylamine (0.63 ml, 0.45 g, 4.5 mmol),1-(3-phenoxyphenyl)-2-propyn-1-ol (prepared as above) (1.0 g, 4.5 mmol)and 4-dimethylaminopyridine (50 mg, 0.4 mmol). The mixture was stirredfor 24 hours at room temperature, concentrated and diluted with 100 mlhexanes. The resulting slurry was filtered through alumina andconcentrated to give 0.90 g (70% of theoretical yield) of the desiredcompound.

Tables 1 and 2 depict representative compounds of this invention,prepared according to a method as described above. Table 1 containscompounds in which R₃ is a substituted or unsubstituted 3-phenoxybenzylmoiety. Table 2 contains compounds in which R₃ represents othermoieties. Nearly all compounds were produced as oils; all structureswere confirmed by spectroscopic analysis.

For convenience, since nearly all compounds in the tables are of thetype in which R₁ is a substituted or unsubstituted phenyl ring, thetables only depict the substituents (if any) on that ring, withH=unsubstituted phenyl, 3-Cl=3-chlorophenyl,3-Cl,4F=3-chloro-4-fluorophenyl, and the like. Naphthyl compounds areindicated as such.

                                      TABLE 1                                     __________________________________________________________________________     ##STR19##                                                                    (R.sub.1 = unsubstituted or substituted phenyl)                               Cmpd.                                                                         No.  Phenyl Subst.                                                                              R.sub.2    R.sub.4                                                                           R.sub.5                                      __________________________________________________________________________    1    3-Cl         CHCl.sub.2 H   H                                            2    4-Cl         i-C.sub.3 H.sub.7                                                                        H   H                                            3    4-Cl         CCl.sub.2 CH.sub.3                                                                       H   H                                            4    2,4-Cl       CHCl.sub.2 H   H                                            5    4-Cl                                                                                        ##STR20## H   H                                            6    4-Cl                                                                                        ##STR21## H   H                                            7    3-Cl         i-C.sub.3 H.sub.7                                                                        H   H                                            8    4-Cl                                                                                        ##STR22## H   H                                            9    3,4-Cl       i-C.sub.3 H.sub.7                                                                        H   H                                            10   3,5-Cl       i-C.sub.4 H.sub.9                                                                        H   H                                            11   4-Cl         C.sub.2 H.sub.5                                                                          H   H                                            12   3-Cl         t-C.sub.4 H.sub.9                                                                        H   H                                            13   2,5-Cl       i-C.sub.3 H.sub.7                                                                        H   H                                            14   3,4-Cl       i-C.sub.3 H.sub.7                                                                        H   H                                            15   4-Cl                                                                                        ##STR23## H   H                                            16   3,5-Cl       i-C.sub.3 H.sub.7                                                                        H   H                                            17   2-Cl         i-C.sub.3 H.sub.7                                                                        H   H                                            18   2,4,5-Cl     i-C.sub.3 H.sub.7                                                                        H   H                                            19   2,4,6-Cl     i-C.sub.3 H.sub.7                                                                        H   H                                            20   3,4,5-Cl     i-C.sub.3 H.sub.7                                                                        H   H                                            21   4-Cl         CN         H   H                                            22   4-Cl         CH(CH.sub.3)OCH.sub.3                                                                    H   H                                            23   4-Cl         i-C.sub.3 H.sub.7                                                                        4-F H                                            24   3-Cl                                                                                        ##STR24## H   H                                            25   3,4-Cl       t-C.sub.4 H.sub.9                                                                        H   H                                            26   4-Cl         sec-C.sub.4 H.sub.9                                                                      H   H                                            27   3,4-Cl       CHClCH.sub.3                                                                             H   H                                            28   2,3-Cl       C.sub.2 H.sub.5                                                                          H   H                                            29   4-Cl         CHCl.sub.2 H   H                                            30   4-Cl         t-C.sub.4 H.sub.9                                                                        H   H                                            31   4-Cl         CH.sub.2 Cl                                                                              H   H                                            32   4-Cl                                                                                        ##STR25## H   H                                            33   4-Cl         CHClCH.sub.3                                                                             H   H                                            34   2-Cl         CHCl.sub.2 H   H                                            35   4-Cl         CF.sub.3   H   H                                            36   3,4-Cl       C.sub.2 H.sub.5                                                                          H   H                                            37   3,4-Cl       i-C.sub.3 H.sub.7                                                                        H   4-F                                          38   3,4-Cl       n-C.sub.3 H.sub.7                                                                        H   H                                            39   3,4-Cl       sec-C.sub.4 H.sub.9                                                                      H   H                                            40   3,4-Cl       i-C.sub.3 H.sub.7                                                                        H   3-F                                          41   H            CHCl.sub.2 H   H                                            42   H            CH.sub.3   H   H                                            43   H            i-C.sub.3 H.sub.7                                                                        H   H                                            44   4-F          CHCl.sub.2 H   H                                            45   4-F                                                                                         ##STR26## H   H                                            46   4-F          i-C.sub.3 H.sub.7                                                                        H   H                                            47   3-F          i-C.sub.3 H.sub.7                                                                        H   H                                            48   4-F          t-C.sub.4 H.sub.9                                                                        H   H                                            49   4-F                                                                                         ##STR27## H   H                                            50   4-F          CHF.sub.2  H   H                                            51   2,3,4,5,6-F  i-C.sub.3 H.sub.7                                                                        H   H                                            52   2,4-F        i-C.sub.3 H.sub.7                                                                        H   H                                            53   4-F          i-C.sub.3 H.sub.7                                                                        4-F H                                            54   3,4-F        i-C.sub.3 H.sub.7                                                                        H   H                                            55   3,5-F        i-C.sub.3 H.sub.7                                                                        H   H                                            56   2,5-F        i-C.sub.3 H.sub.7                                                                        H   H                                            57   2,3,5,6-F    i-C.sub.3 H.sub.7                                                                        H   H                                            58   2,4,5-F      i-C.sub.3 H.sub.7                                                                        H   H                                            59   2,4-F        C.sub.2 H.sub.5                                                                          H   H                                            60   3,4-F        i-C.sub.3 H.sub.7                                                                        H   4-F                                          61   4-CF.sub.3   CHCl.sub.2 H   H                                            62   4-CF.sub.3                                                                                  ##STR28## H   H                                            63   4-OCF.sub.3                                                                                 ##STR29## H   H                                            64   4-OCF.sub.3  CHCl.sub.2 H   H                                            65   2-Cl,4-CF.sub.3                                                                             ##STR30## H   H                                            66   3-CF.sub.3   CHCl.sub.2 H   H                                            67   3-CF.sub.3   i-C.sub.3 H.sub.7                                                                        H   H                                            68   4-CF.sub.3   i-C.sub.3 H.sub.7                                                                        H   H                                            69   2,5-OCH.sub.3                                                                              i-C.sub.3 H.sub.7                                                                        H   H                                            70   4-OCF.sub.3  i-C.sub.3 H.sub.7                                                                        H   H                                            71   3-CF.sub.3,4-Cl                                                                            i-C.sub.3 H.sub.7                                                                        H   H                                            72   2-CF.sub.3   i-C.sub.3 H.sub.7                                                                        H   H                                            73   2-CH.sub.3,3-F                                                                             i-C.sub.3 H.sub.7                                                                        H   H                                            74   2-CH.sub.3,5-F                                                                             i-C.sub.3 H.sub.7                                                                        H   H                                            75   3-F,4-CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                        H   H                                            76   3-OCH.sub.3,5-CF.sub.3                                                                     i-C.sub.3 H.sub.7                                                                        H   H                                            77   3-CF.sub.3,5-F                                                                             i-C.sub.3 H.sub.7                                                                        H   H                                            78   3,5-CF.sub.3 i-C.sub.3 H.sub.7                                                                        H   H                                            79   2-F,4-Br     i-C.sub.3 H.sub.7                                                                        H   H                                            80   3-CF.sub.3   i-C.sub.3 H.sub.7                                                                        4-F H                                            81   3-Cl,4-F     i-C.sub.3 H.sub.7                                                                        H   H                                            82   3-Cl,4-F     i-C.sub.3 H.sub.7                                                                        4-F H                                            83   3-Cl,4-CF.sub.3                                                                            i-C.sub.3 H.sub.7                                                                        H   H                                            84   2-F,5-CF.sub.3                                                                             i-C.sub.3 H.sub.7                                                                        H   H                                            85   3-Cl,4-F     C.sub.2 H.sub.5                                                                          H   H                                            86   3-CF.sub.3                                                                                  ##STR31## H   H                                            87   3-CH.sub.3,4-F                                                                             i-C.sub.3 H.sub.7                                                                        H   H                                            88   3-CF.sub.3   t-C.sub.4 H.sub.9                                                                        H   H                                            89   3-Cl,4-F     i-C.sub.3 H.sub.7                                                                        H   4-F                                          90   3-Cl,4-CH.sub.3                                                                            i-C.sub.3 H.sub.7                                                                        H   H                                            91   3,5-Cl,4-OCH.sub.3                                                                         i-C.sub.3 H.sub.7                                                                        H   H                                            92   2,6-Cl,4-NO.sub.2                                                                          i-C.sub.3 H.sub.7                                                                        H   H                                            93   2-Cl,5-CH.sub.3                                                                            i-C.sub.3 H.sub.7                                                                        H   H                                            94   2-Cl,4-CH.sub.3                                                                            i-C.sub.3 H.sub.7                                                                        H   H                                            95   3-Cl,4-OCH.sub.3                                                                           i-C.sub.3 H.sub.7                                                                        H   H                                            96   2-CH.sub.3,4-Cl                                                                            i-C.sub.3 H.sub.7                                                                        H   H                                            97   2-CH.sub.3,3-Cl                                                                            CHCl.sub.2 H   H                                            98   (4-chloro-alpha-                                                                           CHCl.sub.2 H   H                                                 naphthyl)                                                                99   2,5-OCH.sub.3,4-Cl                                                                         i-C.sub.3 H.sub.7                                                                        H   H                                            100  2-Cl,3,6-OCH.sub.3                                                                         i-C.sub.3 H.sub.7                                                                        H   H                                            101  3,5-Cl,4-CH.sub.3                                                                          i-C.sub.3 H.sub.7                                                                        H   H                                            102                                                                                 ##STR32##   i-C.sub.3 H.sub.7                                                                        H   H                                            103  3-Cl,4-SC.sub.2 H.sub.5                                                                    i-C.sub.3 H.sub.7                                                                        H   H                                            104                                                                                 ##STR33##   i-C.sub.3 H.sub. 7                                                                       H   H                                            105  3-NO.sub.2,4-Cl                                                                            t-C.sub.4 H.sub.9                                                                        H   H                                            106  3-Cl,4-Br    t-C.sub.4 H.sub.9                                                                        H   H                                            107  3-Cl,4-CH.sub.3                                                                            t-C.sub.4 H.sub.9                                                                        H   H                                            108  3-Cl,4-CN    C(CH.sub.3).sub.2 Cl                                                                     H   H                                            109  2-CH.sub.3,4-Cl                                                                            t-C.sub.4 H.sub.9                                                                        H   H                                            110  3-Cl,4-OCH.sub.3                                                                           i-C.sub.3 H.sub.7                                                                        H   4-F                                          111  (4-chloro-alpha-                                                                           C(CH.sub.3).sub.2 Cl                                                                     H   H                                                 naphthyl)                                                                112  3-Cl,4-SO2C.sub.2 H.sub.5                                                                  i-C.sub.3 H.sub.7                                                                        H   H                                                                         H   H                                            113  3-Cl,4-F                                                                                    ##STR34## H   H                                            114  3-(pyrid-2-yloxy)                                                                          i-C.sub.3 H.sub.7                                                                        H   H                                            115  3-Cl,4-F     C.sub.2 H.sub.5                                                                          H   4-F                                          116  3-Cl,4F                                                                                     ##STR35## H   4-F                                          117  3-Cl,4-F     C.sub.2 F.sub.5                                                                          H   H                                            118  3-Cl,4-F     CHBrCH.sub.3                                                                             H   H                                            119  3-Cl,4-F     i-C.sub.3 H.sub.7                                                                        H   2-F                                          120  3-CF.sub.3,4-F                                                                             i-C.sub.3 H.sub.7                                                                        H   4-F                                          121  3-Cl,4-F     n-C.sub.4 H.sub.9                                                                        H   H                                            122  3-Cl,4-F     sec-C.sub.4 H.sub.9                                                                      H   H                                            123  3-Cl,4-F     n-C.sub.3 H.sub.7                                                                        H   H                                            124  3-Cl,4-F                                                                                    ##STR36## H   H                                            125  3-Cl,4-F     i-C.sub.3 H.sub.7                                                                        H   3-F                                          126  3-CN         i-C.sub.3 H.sub.7                                                                        H   H                                            127  3-CH.sub.3,4-Br                                                                            i-C.sub.3 H.sub.7                                                                        H   H                                            128  3-Br         i-C.sub.3 H.sub.7                                                                        H   H                                            129  2,4-F,6-Br   i-C.sub.3 H.sub.7                                                                        H   H                                            130  2,6-Br,4-F   i-C.sub.3 H.sub.7                                                                        H   H                                            131  4-Br         i-C.sub.3 H.sub.7                                                                        H   H                                            132  2-Br         i-C.sub.3 H.sub.7                                                                        H   H                                            133  2-CH.sub.3,4-Br                                                                            i-C.sub.3 H.sub.7                                                                        H   H                                            134  3-Br         t-C.sub.4 H.sub.9                                                                        H   H                                            135  4-Br         t-C.sub.4 H.sub.9                                                                        H   H                                            136  3-I          i-C.sub.3 H.sub.7                                                                        H   H                                            137  4-I          i-C.sub.3 H.sub.7                                                                        H   H                                            138  4-OC.sub.2 H.sub.5                                                                         CHCl.sub.2 H   H                                            139  4-CH.sub.3   CHCl.sub.2 H   H                                            140  4-(t-C.sub.4 H.sub.9)                                                                      CHCl.sub.2 H   H                                            141  4-SCH.sub.3  CHCl.sub.2 H   H                                            142  4-SCH.sub.3  i-C.sub.3 H.sub.7                                                                        H   H                                            143  3-OCH.sub.3  i-C.sub.3 H.sub.7                                                                        H   H                                            144  4-(i-C.sub.3 H.sub.7)                                                                      i-C.sub.3 H.sub.7                                                                        H   H                                            145  2-OCH.sub.3  i-C.sub.3 H.sub.7                                                                        H   H                                            146  2,4-OCH.sub.3                                                                              i-C.sub.3 H.sub.7                                                                        H   H                                            147                                                                                 ##STR37##   i-C.sub.3 H.sub.7                                                                        H   H                                            148  2,3-CH.sub.3 i-C.sub.3 H.sub.7                                                                        H   H                                            149  2-CH.sub.3,4-OCH.sub.3                                                                     i-C.sub.3 H.sub.7                                                                        H   H                                            150  2-OCH.sub.3,5-CH.sub.3                                                                     i-C.sub.3 H.sub.7                                                                        H   H                                            151                                                                                 ##STR38##   i-C.sub.3 H.sub.7                                                                        H   H                                            152  4-(n-C.sub.4 H.sub.9)                                                                      i-C.sub.3 H.sub.7                                                                        H   H                                            153  4-(t-C.sub.4 H.sub.9)                                                                      i-C.sub.3 H.sub.7                                                                        H   H                                            154  3-C.sub.2 H.sub.5                                                                          i-C.sub.3 H.sub.7                                                                        H   H                                            155  3-CH.sub.3   i-C.sub.3 H.sub.7                                                                        H   H                                            156  4-CH.sub.3   i-C.sub.3 H.sub.7                                                                        H   H                                            157  4-C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                          H   H                                            158  3,4-CH.sub.3 i-C.sub.3 H.sub.7                                                                        H   H                                            159  4-C.sub.2 H.sub.5                                                                          i-C.sub.3 H.sub.7                                                                        H   4-F                                          160  4-OCH.sub.3  i-C.sub.3 H.sub.7                                                                        H   H                                            161  4-C.sub.2 H.sub.5                                                                          i-C.sub.3 H.sub.7                                                                        H   H                                            162  3-C.sub.2 H.sub.5                                                                          t-C.sub.4 H.sub.9                                                                        H   H                                            163  4-C.sub.2 H.sub.5                                                                          t-C.sub.4 H.sub.9                                                                        H   H                                            164  4-OC.sub.2 H.sub.5                                                                         t-C.sub.4 H.sub. 9                                                                       H   H                                            165  4-(i-C.sub.3 H.sub.7)                                                                      t-C.sub.4 H.sub.9                                                                        H   H                                            166  3-SCH.sub.3  i-C.sub.3 H.sub.7                                                                        H   H                                            167  3,4-CH.sub.3 t-C.sub.4 H.sub.9                                                                        H   H                                            168                                                                                 ##STR39##   t-C.sub.4 H.sub.9                                                                        H   H                                            169  3,4-OCH.sub.3                                                                              i-C.sub.3 H.sub.7                                                                        H   H                                            170                                                                                 ##STR40##   i-C.sub.3 H.sub.7                                                                        H   H                                            171  3-OC.sub.2 H.sub.5                                                                         i-C.sub.3 H.sub.7                                                                        H   H                                            172  4-CN         i-C.sub.3 H.sub.7                                                                        H   H                                            173  4-NO.sub.2   CHCl.sub.2 H   H                                            174  3-NO.sub.2   CHCl.sub.2 H   H                                            175  3-NO.sub.2   t-C.sub.4 H.sub.9                                                                        H   H                                            176  3,4-(OCH.sub.2 O)                                                                          i-C.sub.3 H.sub.7                                                                        H   4-F                                          177  3,4-(OCH.sub.2 O)                                                                           ##STR41## H   H                                            178  3,4-(OCH.sub.2 O)                                                                          C.sub.2 H.sub.5                                                                          H   H                                            179  3,4-(OC.sub.2 H.sub.4 O)                                                                   i-C.sub.3 H.sub.7                                                                        H   H                                            180  3,4-(OCH.sub.2 O)                                                                          i-C.sub.3 H.sub.7                                                                        H   H                                            181  3,4-(OCH.sub.2 O)                                                                          i-C.sub.3 H.sub.7                                                                        4-F H                                            182  3,4-[OC(CH.sub.3 ).sub.2 O]                                                                i-C.sub.3 H.sub.7                                                                        H   H                                            183  3,4-(OCH.sub.2 O)                                                                          i-C.sub.3 H.sub.7                                                                        H   2-F                                          184  4-OCH.sub.3  n-C.sub.3 H.sub.7                                                                        H   H                                            185  3,4-(OCH.sub.2 O)                                                                          sec-C.sub.4 H.sub.9                                                                      H   H                                            186  4-C.sub.6 H.sub.5                                                                          i-C.sub.3 H.sub.7                                                                        H   H                                            187  3,4-(CH.sub.2 CH.sub.2 CH.sub.2)                                                           i-C.sub.3 H.sub.7                                                                        H   H                                            188  3-4-(OCH.sub.2 O)                                                                          n-C.sub.3 H.sub.7                                                                        H   H                                            189  4-Cl         i-C.sub.3 H.sub.7                                                                        H   4-F                                          190  3,4-(OCH.sub.2 O)                                                                          i-C.sub.3 H.sub.7                                                                        H   2-F                                          191  3-Cl,4-F     i-C.sub.3 H.sub.7                                                                        H   2,4-F                                        192  3-CF.sub.3   i-C.sub.3 H.sub.7                                                                        H   3-F                                          193  3-CF.sub.3,4-Cl                                                                            i-C.sub.3 H.sub.7                                                                        H   4-F                                          194  3-Cl         i-C.sub.3 H.sub.7                                                                        H   4-F                                          195  3-CF.sub.3,4-Cl                                                                            i-C.sub.3 H.sub.7                                                                        H   3-F                                          196  3-Cl,4-F     i-C.sub.3 H.sub.7                                                                        H   4-CN                                         197  4-F          i-C.sub.3 H.sub.7                                                                        H   4-F                                          198  2,3,4,5,6-F  i-C.sub.3 H.sub.7                                                                        H   4-F                                          199  3,5-F        i-C.sub.3 H.sub.7                                                                        H   4-F                                          200  3-F          i-C.sub.3 H.sub.7                                                                        H   4-F                                          201  3-OCH.sub.3  i-C.sub.3 H.sub.7                                                                        H   4-F                                          202  3-CF.sub.3   i-C.sub.3 H.sub. 7                                                                       H   4-F                                          203  3-Cl,4-F     i-C.sub.3 H.sub.7                                                                        H   3-Cl                                         204  3-Cl,4-F     t-C.sub.4 H.sub.9                                                                        H   4-F                                          205  4-F          i-C.sub.3 H.sub.7                                                                        H   3-Cl                                         206  4-F          i-C.sub.3 H.sub.7                                                                        H   2,4-F                                        207  3,4-Cl       i-C.sub.3 H.sub.7                                                                        H   3-Cl                                         208  4-CN         i-C.sub.3 H.sub.7                                                                        H   3-Cl                                         209  2,4-F        i-C.sub.3 H.sub.7                                                                        H   4-F                                          210  3-Cl,4-F     sec-C.sub.4 H.sub.9                                                                      H   4-F                                          211  3,4-Cl       sec-C.sub.4 H.sub.9                                                                      H   4-F                                          212  3,4-F        i-C.sub.3 H.sub.7                                                                        H   4-CN                                         213  3,4-Cl       i-C.sub.3 H.sub.7                                                                        H   2,4-F                                        214  3,4-F        i-C.sub.3 H.sub.7                                                                        H   2,4-F                                        215  3-Cl,4-F     i-C.sub.3 H.sub.7                                                                        H   3,5-F                                        216  3-Cl,4-F     i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          217  3-Cl,4-F     i-C.sub.3 H.sub.7                                                                        H   3,4-F                                        218  3,4-Cl       i-C.sub.3 H.sub.7                                                                        H   3,4-F                                        219  3-4-[OC(CH.sub.3).sub.2 O]                                                                 i-C.sub.3 H.sub.7                                                                        H   4-F                                          220  4-F          i-C.sub.3 H.sub.7                                                                        H   4-OCH.sub.3                                  221  3-Cl,4-F     i-C.sub.3 H.sub.7                                                                        H   4-OCH.sub.3                                  222  3-F,4-CN     i-C.sub.3 H.sub.7                                                                        H   4-F                                          223  3,4-Cl       i-C.sub.3 H.sub.7                                                                        H   4-OCH.sub.3                                  224  3-Cl,4-F     C(CH.sub.3).sub.2 Cl                                                                     H   4-F                                          225  3-Cl,4-F     i-C.sub.3 H.sub.7                                                                        H   4-CH.sub. 3                                  226  4-Br         i-C.sub.3 H.sub.7                                                                        H   4-F                                          227  4-CN         i-C.sub.3 H.sub.7                                                                        H   4-F                                          228  4-(i-C.sub.3 H.sub.7)                                                                      i-C.sub.3 H.sub.7                                                                        H   4-F                                          229  3-Br         i-C.sub.3 H.sub.7                                                                        H   4-F                                          230  3-Cl,4-F     i-C.sub.3 H.sub.7                                                                        6-F 4-F                                          231  4-F          i-C.sub.3 H.sub.7                                                                        H   4-CH.sub.3                                   232  2,3,4,5,6-F  i-C.sub.3 H.sub.7                                                                        H   2,4-F                                        233  3-F,4-CN     i-C.sub.3 H.sub.7                                                                        H   H                                            234  4-I          i-C.sub.3 H.sub.7                                                                        H   4-F                                          235  4-(t-C.sub.4 H.sub.9)                                                                      i-C.sub.3 H.sub.7                                                                        H   4-F                                          236  3-CH.sub.3,4-F                                                                             i-C.sub.3 H.sub.7                                                                        H   4-F                                          237  4-Cl         i-C.sub.3 H.sub.7                                                                        H   4-Br                                         238  3-Cl,4-F     i-C.sub.3 H.sub.7                                                                        H   4-Br                                         239  3-Cl,4-F     i-C.sub.3 H.sub.7                                                                        H   4-Cl                                         240  3,4-(OCH.sub.2 O)                                                                          i-C.sub.3 H.sub.7                                                                        H   4-Cl                                         241  3,4-[OC(CH.sub.3).sub.2 O]                                                                 i-C.sub.3 H.sub.7                                                                        H   4-Cl                                         242  3,4-[OC(CH.sub.3).sub.2 O]                                                                 i-C.sub.3 H.sub.7                                                                        4-F H                                            243  3,4-(CH.sub.2 CH.sub.2 O)                                                                  I-C.sub.3 H.sub.7                                                                        H   H                                            244  3,4-(OCF.sub.2 O)                                                                          i-C.sub.3 H.sub.7                                                                        H   4-F                                          245  3,4-(OCF.sub.2 O)                                                                          i-C.sub.3 H.sub.7                                                                        H   H                                            246  3,4-(OCH.sub.2 O)                                                                          i-C.sub.3 H.sub.7                                                                        H   4-CF.sub.3                                   247  3-Cl,4-F     i-C.sub.3 H.sub.7                                                                        H   4-CF.sub.3                                   248  3,4,5-OCH.sub.3                                                                            i-C.sub.3 H.sub.7                                                                        H   H                                            249  2,3-CH.sub.3 i-C.sub.3 H.sub.7                                                                        H   H                                            250  2,5-CH.sub.3 i-C.sub.3 H.sub.7                                                                        H   H                                            251  3,4-Br       i-C.sub.3 H.sub.7                                                                        H   4-F                                          252  3,4-Br       i-C.sub.3 H.sub.7                                                                        H   H                                            253  3-Br,4-F     i-C.sub.3 H.sub.7                                                                        H   4-F                                          254  3-Br,4-F     i-C.sub.3 H.sub.7                                                                        H   H                                            255  3-I          i-C.sub.3 H.sub.7                                                                        H   4-F                                          256  3-Cl,4-F     i-C.sub.3 H.sub.7                                                                        H   4-SCH.sub.3                                  257  4-F          i-C.sub.3 H.sub.7                                                                        H   4-SCH.sub.3                                  258  3-Cl,4-F     C.sub.2 F.sub.5                                                                          H   4-F                                          259  4-F          i-C.sub.3 H.sub.7                                                                        H   4-Br                                         260  3-Cl         i-C.sub.3 H.sub.7                                                                        H   4-Br                                         261  3-Cl,4-F     sec-C.sub.4 H.sub.9                                                                      4-F H                                            262  3-Cl,4-F     i-C.sub.3 H.sub.7                                                                        2-F 4-F                                          263  2-CH.sub.3,5-Cl                                                                            i-C.sub.3 H.sub.7                                                                        H   H                                            264  2-OCH.sub.3,5-Cl                                                                           i-C.sub.3 H.sub.7                                                                        H   H                                            265  4-F          i-C.sub.3 H.sub.7                                                                        H   3,4-F                                        266  3-CF.sub.3   i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         267  3-Cl,4-F     i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         268  3-CF.sub. 3  i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          269  4-Cl         i-C.sub.3 H.sub.7                                                                        H   4-Cl                                         270  3-Cl         i-C.sub.3 H.sub.7                                                                        H   4-Cl                                         271  3-NO.sub.2   i-C.sub.3 H.sub.7                                                                        H   4-Cl                                         272  3-SCF.sub.3  i-C.sub.3 H.sub.7                                                                        H   4-F                                          273  3-Br,4-F     i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          274  3,4-(OCH.sub.2 O)                                                                          i-C.sub.3 H.sub.7                                                                        6-Cl                                                                              4-F                                          275  3,4-F        i-C.sub.3 H.sub.7                                                                        H   4-Br                                         276  3-Br,4-F     i-C.sub.3 H.sub.7                                                                        H   4-Br                                         277  3-CF.sub.3,4-F                                                                             i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          278  3,4-F        i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          279  3-I          i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          280                                                                                 ##STR42##   i-C.sub.3 H.sub.7                                                                        H   4-F                                          281  3-I,4-F      i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          282  3-F,4-Br     i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          283  3,4-[OC(CH.sub.3).sub.2 O]                                                                 i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          284  3,4-(OCF.sub.2 O)                                                                          i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          285  3,4-(OCF.sub.2 O)                                                                          i-C.sub.3 H.sub.7                                                                        4-F H                                            286  4-OCF.sub.3  i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          287  4-CF.sub.3   i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          288  3-OCF.sub.2 CHF.sub.2                                                                      i-C.sub. 3 H.sub.7                                                                       H   4-F                                          289  3,4-Cl       i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          290  4-Cl         CH(C.sub.2 H.sub.5).sub.2                                                                H   4-F                                          291  3-CF.sub.3   CH(C.sub.2 H.sub.5).sub.2                                                                H   4-F                                          292  2,4-Cl,5-F   i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          293  3-NO.sub.2,4-F                                                                             i-C.sub.3 H.sub.7                                                                        H   H                                            294  3-CF.sub.3                                                                                  ##STR43## H   4-F                                          295  3,4-F        i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         296  3,4-Cl       i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         297  3-CF.sub.3,4-F                                                                             i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         298  3-Br,4-F     i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         299  3-Br,4-F     i-C.sub.3 H.sub.7                                                                        4-F H                                            300  3-CF.sub.3,4-F                                                                             i-C.sub.3 H.sub.7                                                                        4-F H                                            301  4-(t-C.sub.4 H.sub.9)                                                                      i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         302  3-NO.sub.2   i-C.sub.3 H.sub.7                                                                        H   H                                            303  2-Cl,5-F     i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          304  2,3,5,6-F    i-C.sub.3 H.sub.7                                                                        H   4-F                                          305  3-Cl,4-F     CHBrCH.sub.3                                                                             H   4-F                                          306  3,4-(OCH.sub.2 O)                                                                          CHBrCH.sub.3                                                                             H   H                                            307  3-CF.sub.3,4-NO2                                                                           i-C.sub.3 H.sub.7                                                                        H   H                                            308  3-Cl,4-(t-C.sub.4 H.sub.9)                                                                 i-C.sub.3 H.sub.7                                                                        H   4-F                                          309  3-Cl,4-F     CF(CH.sub.3).sub.2                                                                       H   4-F                                          310  3-Cl,4-F     CF(CH.sub.3).sub.2                                                                       4-F 4-F                                          311  2,4-Cl       i-C.sub.3 H.sub.7                                                                        H   H                                            312  2,4-Cl       i-C.sub.3 H.sub.7                                                                        H   4-F                                          313  3,4-(OCH.sub.2 O)                                                                          i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         314  4-CF.sub.3   i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          315  3-Cl,4-F     CF(CH.sub.3).sub.2                                                                       H   2,4-F                                        316  3-Cl,4-F     CF(CH.sub.3).sub.2                                                                       6-F 4-F                                          317  4-(i-C.sub.3 H.sub.7)                                                                      sec-C.sub.4 H.sub.9                                                                      H   H                                            318  3,4-F        CF(CH.sub.3).sub.2                                                                       H   4-F                                          319  3-CF.sub.3   CF(CH.sub.3).sub.2                                                                       H   4-F                                          320  4-(i-C.sub.3 H.sub.7)                                                                      C.sub.2 H.sub.5                                                                          H   4-F                                          321  4-(i-C.sub.3 H.sub.7)                                                                      CH(C.sub.2 H.sub.5).sub.2                                                                H   H                                            322  4-(i-C.sub.3 H.sub.7)                                                                      t-C.sub.4 H.sub.9                                                                        H   4-F                                          323  4-OCF.sub.3  i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         324  4-CF.sub.3   i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         325  4-F          i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         326  3-I,4-F      i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         327  3-Cl,4-F     i-C.sub.3 H.sub.7                                                                        5-F 4-F                                          328  3-Cl,4-CF.sub.3                                                                            i-C.sub.3 H.sub.7                                                                        5-F 4-F                                          329  4-(i-C.sub.3 H.sub.7)                                                                      i-C.sub.4 H.sub.9                                                                        H   4-F                                          330  2,4-F,3-Cl   i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          331  2,4-F,3-Cl   i-C.sub.3 H.sub.7                                                                        H   4-Cl                                         332  2,4-F,3-Cl   i-C.sub.3 H.sub.7                                                                        H   H                                            333  4-Br         i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          334  3-I,4-F      i-C.sub.3 H.sub.7                                                                        4-F H                                            335  4-I          i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          336  3,4-F        i-C.sub.3 H.sub.7                                                                        4-F H                                            337  4-CF.sub.3   i-C.sub.3 H.sub.7                                                                        4-F H                                            338  4-OCF.sub.3  i-C.sub.3 H.sub.7                                                                        4-F H                                            339  4-(i-C.sub.3 H.sub.7)                                                                       ##STR44## H   H                                            340  3-CF.sub.3,4-Cl                                                                            i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          341  3-Cl         i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          342  3-F          i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          343  3-Cl,4-F     i-C.sub.3 H.sub.7                                                                        4,6-F                                                                             4-F                                          344  4-(t-C.sub.4 H.sub.9)                                                                      i-C.sub.3 H.sub.7                                                                        H   4-CH.sub.3                                   345  4-(t-C.sub.4 H.sub.9)                                                                      i-C.sub.3 H.sub.7                                                                        H   4-OCH.sub.3                                  346  3-Cl,4-F     i-C.sub.3 H.sub.7                                                                        4-F 3,4-F                                        347  4-OCF.sub.3  i-C.sub.3 H.sub.7                                                                        4-F 3,4-F                                        348  2,3,4-F      i-C.sub.3 H.sub.7                                                                        H   4-F                                          349  2,3,4-F      i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          350  3-(t-C.sub.4 H.sub.9)                                                                      i-C.sub.3 H.sub.7                                                                        H   4-F                                          351  2-F,4-Br     i-C.sub.3 H.sub.7                                                                        H   4-F                                          352  2,4-F,3-Cl   i-C.sub.3 H.sub.7                                                                        H   4-F                                          353  4-SCH.sub.3  i-C.sub.3 H.sub.7                                                                        4-F H                                            354  3-F,4-CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                        4-F H                                            355  3-F,4-CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          356  3-Cl,4-CH.sub.3                                                                            i-C.sub.3 H.sub.7                                                                        4-F H                                            357  3-Cl,4-CH.sub.3                                                                            i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          358  3-CH.sub.3,4-Br                                                                            i-C.sub.3 H.sub.7                                                                        4-F H                                            359  3-CH.sub.3,4-Br                                                                            i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          360  4-C.sub.2 H.sub.5                                                                          i-C.sub.3 H.sub.7                                                                        4-F H                                            361  4-C.sub.2 H.sub.5                                                                          i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          362  3-SCH.sub.3  i-C.sub.3 H.sub.7                                                                        4-F H                                            363  3,4-OCH.sub.3                                                                              i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          364  3-CF3,4-Br   i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          365  4-CF3        i-C.sub.3 H.sub.7                                                                        H   4-Cl                                         366  3,4-(OCH.sub.2 O)                                                                          i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         367  3,4-(OCH.sub.2 O)                                                                          i-C.sub.3 H.sub.7                                                                        H   4-(t-C.sub.4 H.sub.9)                        368  3-Cl,4-OC.sub.2 H.sub.5                                                                    i-C.sub.3 H.sub.7                                                                        H   H                                            369  3-Cl,4-OC.sub.2 H.sub.5                                                                    i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         370  3-Cl,4-OC.sub.2 H.sub.5                                                                    i-C.sub.3 H.sub.7                                                                        4-F H                                            371  4-OC.sub.2 H.sub.5                                                                         i-C.sub.3 H.sub.7                                                                        H   H                                            372  4-OC.sub.2 H.sub.5                                                                         i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         373  4-OC.sub.2 H.sub.5                                                                         i-C.sub.3 H.sub.7                                                                        4-F H                                            374  3-Cl,4-I     i-C.sub.3 H.sub.7                                                                        H   4-F                                          375  3-F          i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         376  3,4-Cl       i-C.sub.3 H.sub.7                                                                        4-F H                                            377  3-Br,4-CF.sub.3                                                                            i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         378  4-Br         i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         379  3-Br,4-F     i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         380  3-Cl,4-Br    1-C.sub.3 H.sub.7                                                                        H   4-Cl                                         381  3-Cl,4-Br    i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         382  3-Cl,4-Br    i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          383  3,4-Br       i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          384  3,4-Br       i-C.sub.3 H.sub.7                                                                        4-F H                                            385  3-Cl,4-I     i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          386  3-Br         i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         387  3-Br         i-C.sub.3 H.sub.7                                                                        4-F H                                            388  3-CF.sub.3,4-Cl                                                                            i-C.sub.3 H.sub.7                                                                        4-F H                                            389  3-I          i-C.sub.3 H.sub.7                                                                        H   4-Cl                                         390  3-Cl         i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         391  4-Cl         i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         392  4-CN         i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         393  4-CN         i-C.sub.3 H.sub.7                                                                        H   4-Cl                                         394  4-CN         i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          395  2,4-F,3-Cl   i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         396  3-CH.sub.3,4-F                                                                             i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          397  3-CH.sub.3,4-F                                                                             i-C.sub.3 H.sub.7                                                                        H   4-Cl                                         398  3-Br,4-F     i-C.sub.3 H.sub.7                                                                        H   4-Cl                                         399  3-CH.sub.3,4-F                                                                             i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         400  3-CH.sub.3,4-F                                                                             i-C.sub.3 H.sub.7                                                                        4-F H                                            401  3-CH.sub.3   i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         402  3-Cl,4-CH.sub.3                                                                            i-C.sub.3 H.sub.7                                                                        H   4-F                                          403  3-Cl,4-CH.sub.3                                                                            i-C.sub.3 H.sub.7                                                                        H   4-Cl                                         404  3-Cl,4-CH.sub.3                                                                            i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         405  3-CH.sub.3   i-C.sub.3 H.sub.7                                                                        H   4-F                                          406  3,4-CH.sub.3 i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         407  3-CH.sub.3,4-Br                                                                            i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         408  3-Cl,4-OCH.sub.3                                                                           i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          409  3-Cl,4-OCH.sub.3                                                                           i-C.sub.3 H.sub.7                                                                        4-F H                                            410  3-Cl,4-OCH.sub.3                                                                           i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         411  2-C.sub.2 H.sub.5                                                                          i-C.sub.3 H.sub.7                                                                        H   4-F                                          412  4-OCH.sub.3  i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         413  3-I,4-F      i-C.sub.3 H.sub.7                                                                        H   4-Cl                                         414  4-SO.sub.2 CH.sub.3                                                                        i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          415  3-Cl,4-F     C(CH.sub.3)CH.sub.2                                                                      4-F 4-Cl                                         416  3-Cl,4-F     C(CH.sub.3)CH.sub.2                                                                      4-F H                                            417  3-Cl,4-F     C(CH.sub.3) CH.sub.2                                                                     H   H                                            418  4-OCF.sub.2 CHFCl                                                                          i-C.sub.3 H.sub.7                                                                        H   H                                            419  4-OCF.sub.2 CHFCl                                                                          i-C.sub.3 H.sub.7                                                                        4-F H                                            420  3-Cl,4-OCH.sub.2 CF.sub.3                                                                  i-C.sub.3 H.sub.7                                                                        H   4-F                                          421  3-Cl,4-OCH.sub.2 CF.sub.3                                                                  i-C.sub.3 H.sub.7                                                                        H   4-Cl                                         422  4-OCH.sub.2 CF.sub.3                                                                       i-C.sub.3 H.sub.7                                                                        4-F H                                            423  4-OCH.sub.2 CF.sub.3                                                                       i-C.sub.3 H.sub.7                                                                        H   H                                            424  3-Cl,4-OCH.sub.2 CF.sub.3                                                                  i-C.sub.3 H.sub.7                                                                        4-F H                                            425  3-Cl,4-OCH.sub.2 CF.sub.3                                                                  i-C.sub.3 H.sub.7                                                                        H   H                                            426  3-OC.sub.2 H.sub.5                                                                         i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          427  2-Cl,4-CF.sub.3                                                                            i-C.sub.3 H.sub.7                                                                        H   4-F                                          428  2-Cl,4-CF.sub.3                                                                            i-C.sub.3 H.sub.7                                                                        4-F H                                            429  3-F,4-OCH.sub.2 CF.sub.3                                                                   i-C.sub.3 H.sub.7                                                                        H   Cl                                           430  4-CF.sub.3   C(CH.sub.3)CH.sub.2                                                                      H   H                                            431  4-CF.sub.3   C(CH.sub.3)CH.sub.2                                                                      4-F H                                            432  4-CF.sub.3   C(CH.sub.3)CH.sub.2                                                                      4-F 4-Cl                                         433  3-Br,4-CF.sub.3                                                                            i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         434  3-Br,4-CF.sub.3                                                                            i-C.sub.3 H.sub.7                                                                        4-F H                                            435  3-F,4-OCH.sub.3                                                                            i-C.sub.3 H.sub.7                                                                        4-F H                                            436  3-OCF.sub.3  i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         437  3-OCF.sub.3  i-C.sub.3 H.sub.7                                                                        4-F H                                            438  3-Cl,4-C2H5  i-C.sub.3 H.sub.7                                                                        H   4-F                                          439  3-F,4-OC2H5  i-C.sub.3 H.sub.7                                                                        4-F H                                            440  4-n-C.sub.3 H.sub.7                                                                        i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          441  3-F,4-Cl     i-C.sub.3 H.sub.7                                                                        4-F 4-F                                          442  4-CF.sub.3   C(CH.sub.3)CH.sub.2                                                                      H   4-F                                          443  4-CF.sub.3                                                                                  ##STR45## 4-F H                                            444  4-CF.sub.3                                                                                  ##STR46## 4-F 4-Cl                                         445  2-NO.sub.2,4-CF.sub.3                                                                      i-C.sub.3 H.sub.7                                                                        4-F H                                            446  3-Br,4-OC.sub.2 H.sub.5                                                                    i-C.sub.3 H.sub.7                                                                        H   4-F                                          447  3-Cl,4-F     i-C.sub.3 H.sub.7                                                                        H   4-I                                          448  3-Cl,4-F     i-C.sub.3 H.sub.7                                                                        4-Cl                                                                              4-F                                          449  3-I,4-F      i-C.sub.3 H.sub.7                                                                        H   4-F                                          450  3,4-(OCF.sub.2 O)                                                                          i-C.sub.3 H.sub.7                                                                        H   4-Cl                                         451  2,4-F,3-Cl   i-C.sub.3 H.sub.7                                                                        4-F H                                            452  3-OCH.sub.2 CF.sub.3,4-Cl                                                                  i-C.sub.3 H.sub.7                                                                        4-F 4-Cl                                         __________________________________________________________________________

                                      TABLE 2                                     __________________________________________________________________________     ##STR47##                                                                    (R.sub.1 = unsubstituted or substituted phenyl)                               Cmpd.                                                                         No. Phenyl Subst.                                                                           R.sub.2  R.sub.3                                                __________________________________________________________________________    453 4-Cl      CHCl.sub.2                                                                              ##STR48##                                             454 2,3-Cl    CHCl.sub.2                                                                              ##STR49##                                             455 4-Cl      i-C.sub.3 H.sub.7                                                                       ##STR50##                                             456 4-F       i-C.sub.3 H.sub.7                                                                       ##STR51##                                             457 4-Cl      i-C.sub.3 H.sub.7                                                                       ##STR52##                                             458 4-F       i-C.sub.3 H.sub.7                                                                       ##STR53##                                             459 3-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR54##                                             460 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR55##                                             461 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR56##                                             462 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR57##                                             463 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR58##                                             464 3,4(OCH.sub.2 O)                                                                        i-C.sub.3 H.sub.7                                                                       ##STR59##                                             465 3,4(OCH.sub.2 O)                                                                        i-C.sub.3 H.sub.7                                                                       ##STR60##                                             466 3,4(OCH.sub.2 O)                                                                        i-C.sub.3 H.sub.7                                                                       ##STR61##                                             467 3,4(OCH.sub.2 O)                                                                        i-C.sub.3 H.sub.7                                                                       ##STR62##                                             468 3,4[OC(CH.sub.3)2O]                                                                     i-C.sub.3 H.sub.7                                                                       ##STR63##                                             469 3-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR64##                                             470 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR65##                                             471 3-Cl,4-I  i-C.sub.3 H.sub.7                                                                       ##STR66##                                             472 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR67##                                             473 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR68##                                             474 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR69##                                             475 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR70##                                             476 3-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR71##                                             477 3-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR72##                                             478 4-Br      i-C.sub.3 H.sub.7                                                                       ##STR73##                                             479 3-Cl-4-F  i-C.sub.3 H.sub.7                                                                       ##STR74##                                             480 3-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR75##                                             481 3,4-Cl    i-C.sub.3 H.sub.7                                                                       ##STR76##                                             482 3-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR77##                                             483 3,4(OCH.sub.2 O)                                                                        i-C.sub.3 H.sub.7                                                                       ##STR78##                                             484 4-Cl      i-C.sub.3 H.sub.7                                                                       ##STR79##                                             485 3,4-F     i-C.sub.3 H.sub.7                                                                       ##STR80##                                             486 2,4-F     i-C.sub.3 H.sub.7                                                                       ##STR81##                                             487 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR82##                                             488 3-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR83##                                             489 3-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR84##                                             490 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR85##                                             491 4-F       i-C.sub.3 H.sub.7                                                                       ##STR86##                                             492 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR87##                                             493 3-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR88##                                             494 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR89##                                             495 3-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR90##                                             496 4-(t-C.sub.4 H.sub.9)                                                                   i-C.sub.3 H.sub.7                                                                       ##STR91##                                             497 4-(t-C.sub.4 H.sub.9)                                                                   i-C.sub.3 H.sub.7                                                                       ##STR92##                                             498 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR93##                                             499 3-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR94##                                             500 2,4-F,3-Cl                                                                              i-C.sub.3 H.sub.7                                                                       ##STR95##                                             501 3,4(OCH.sub.2 O)                                                                        i-C.sub.3 H.sub.7                                                                       ##STR96##                                             502 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR97##                                             503 3-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR98##                                             504 4-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR99##                                             505 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR100##                                            506 3-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR101##                                            507 3-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR102##                                            508 3-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR103##                                            509 3-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR104##                                            510 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR105##                                            511 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR106##                                            512 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR107##                                            513 3-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR108##                                            514 3,4-Cl    i-C.sub.3 H.sub.7                                                                       ##STR109##                                            515 3,4(OCH.sub.2 O)                                                                        i-C.sub.3 H.sub.7                                                                       ##STR110##                                            516 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR111##                                            517 3-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR112##                                            518 3-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR113##                                            519 3-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR114##                                            520 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR115##                                            521 2,4-F,3-Cl                                                                              i-C.sub.3 H.sub.7                                                                       ##STR116##                                            522 2,4-F,3-Cl                                                                              i-C.sub.3 H.sub.7                                                                       ##STR117##                                            523 3,4-Cl    i-C.sub.3 H.sub.7                                                                       ##STR118##                                            524 3,4-F     C.sub.2 H.sub.5                                                                         ##STR119##                                            525 3,4-F     t-C.sub.4 H.sub.9                                                                       ##STR120##                                            526 3,4-F     CH.sub.3                                                                                ##STR121##                                            527 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR122##                                            528 3-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR123##                                            529 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR124##                                            530 4-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR125##                                            531 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR126##                                            532 3,4(OCH.sub.2 O)                                                                        i-C.sub.3 H.sub.7                                                                       ##STR127##                                            533 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR128##                                            534 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR129##                                            535 4-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR130##                                            536 4-(t-C.sub.4 H.sub.9)                                                                   i-C.sub.3 H.sub.7                                                                       ##STR131##                                            537 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR132##                                            538 4-OCF.sub.3                                                                             i-C.sub.3 H.sub.7                                                                       ##STR133##                                            539 4-NO2     i-C.sub.3 H.sub.7                                                                       ##STR134##                                            540 3,4(OCH.sub.2 O)                                                                        i-C.sub.3 H.sub.7                                                                       ##STR135##                                            541 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR136##                                            542 4-OCF.sub.3                                                                             i-C.sub.3 H.sub.7                                                                       ##STR137##                                            543 4-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR138##                                            544 4-(t-C.sub.4 H.sub.9)                                                                   i-C.sub.3 H.sub.7                                                                       ##STR139##                                            545 3-CH.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR140##                                            546 3-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR141##                                            547 3,4-(OCH.sub.2 O)                                                                       i-C.sub.3 H.sub.7                                                                       ##STR142##                                            548 3-CF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                       ##STR143##                                            549 3-Cl,4-F  i-C.sub.3 H.sub.7                                                                       ##STR144##                                            550 4-OCF.sub.3                                                                             i-C.sub.3 H.sub.7                                                                       ##STR145##                                            551 3-F,4-Br  i-C.sub.3 H.sub.7                                                                       ##STR146##                                            552 4-C.sub.2 H.sub.5                                                                       i-C.sub.3 H.sub.7                                                                       ##STR147##                                            553 4-Cl      i-C.sub.3 H.sub.7                                                                       ##STR148##                                            554 4-Cl      i-C.sub.3 H.sub.7                                                                       ##STR149##                                            555 3-CF.sub.3,4-Cl                                                                         i-C.sub.3 H.sub.7                                                                       ##STR150##                                            556 3,4-OCF.sub. 2 O                                                                        i-C.sub.3 H.sub.7                                                                       ##STR151##                                            557 3-Br      i-C.sub.3 H.sub.7                                                                       ##STR152##                                            558 3-Br,4-F  i-C.sub.3 H.sub.7                                                                       ##STR153##                                            559 3,4-F     i-C.sub.3 H.sub.7                                                                       ##STR154##                                            560 4-CF.sub.3                                                                              C(CH.sub.3)CH.sub.2                                                                     ##STR155##                                            __________________________________________________________________________

INSECTICIDAL EVALUATION TESTS

The compounds in Tables 1 and 2 above were tested for insecticidalactivity using the following testing procedures. LC₅₀ values, based onthe results of these tests and calculated according to dosage-mortalitycurves, are expressed in Table 3.

Housefly [Musca domestica]:

Test compounds were diluted in acetone and aliquots pipetted onto thebottom of aluminum dishes. To ensure even spreading of the chemical onthe bottom of the dishes, 1 ml of acetone containing 0.01% peanut oilwas also added to each dish. After all solvents had evaporated, thedishes were placed in circular cardboard cages containing 25 femalehouseflies, 1-2 days old. The cages were covered on the bottom withcellophane and on the top with tulle netting, and each contained asugar-water saturated cotton plug for maintenance of the flies.Mortality was recorded after 48 hours. Test levels ranged from 100 μg/25female houseflies downward. The LC-50 value is expressed below in Table3 under the heading "HF", in terms of μg of the test compound per 25female flies.

Black Bean Aphid [Aphis fabae (Scop.)]:

Nasturtium plants (Tropaeolum sp.) approximately 5 cm tall, weretransplanted into sandy loam soil in small cups and infested with 25-50black bean aphids of mixed ages. Twenty-four hours later they weresprayed to the point of runoff with 50-50 acetone-water solutions of thetest compounds. Treated plants were held in the greenhouse and mortalitywas recorded after 48 hours. Test concentrations ranged from 0.05%downward. The LC-50 value is expressed below in Table 3 under theheading "BBA" in terms of percent of the test compound in the sprayedsolution.

Tobacco Budworm [Heliothis virescens (Fabricius)]:

(a) Contact: Test compounds were diluted in a 50-50 acetone-watersolution. Cotton (Gossypium sp.) cotyledons were immersed in the testsolutions for 2-3 seconds and placed on a wire screen to dry. The driedleaves were placed in petri dishes containing a moistened piece offilter paper and infested with 5 second-instar tobacco budworm larvae.The dishes were placed in a high humidity chamber for 5 days, andpercent mortality of the larvae recorded. Test concentrations rangedfrom 0.1% downward. The LC-50 values are expressed below in Table 3under the heading "TBW-C" in terms of percent of the test compound inthe solution.

(b). Eggs: Paper towel patches of 2-day old eggs of the tobacco budwormwere dipped in acetone solutions of the test compound and placed inpetri dishes containing a portion of larval rearing medium. Treated eggswere maintained at 78° F. and mortality was recorded after all controleggs had hatched and the young larvae were feeding on the media. Testconcentrations ranged from 0.1% downward. The LC-50 value is expressedbelow in Table 3 under the heading "TBW-E" in terms of percent of thetest compound in the solution.

Cabbage Looper [Trichoplusia ni (Hubner)]:

Test compounds were diluted in a 50-50 acetone-water solution.Cotyledons of hyzini squash (Calabacita abobrinha), approximately 1×1.5inches, were immersed in the test solutions for 2-3 seconds and placedon a wire screen to dry. The dried leaves were placed in petri dishescontaining a moistened piece of filter paper and infested with 5second-instar cabbage looper larvae. The dishes were placed in a highhumidity chamber. Mortality of the larvae was recorded 3-5 days later.Test concentrations ranged from 0.1% downward. The LC-50 value isexpressed below in Table 3 under the heading "CL" in terms of percent ofthe test compound in solution.

Beet Armyworm (Spodoptera exigua):

Test compounds were diluted in a 50-50 acetone-water solution. Youngleaves of sugar beets (Beta vulgaris) were immersed in the testsolutions for 2-3 seconds and placed on a wire screen to dry. The driedleaves were placed in petri dishes containing a moistened filter paperand infested with five second-instar beet armyworm larvae. The disheswere placed in a high humidity chamber. Mortality of the larvae wasrecorded five days later. Test concentrations ranged from 0.1% downward.The LC-50 values are expressed below in Table 3 under the heading "BAW"in terms of percent of the test compound in solution.

Aster Leafhopper [Macrosteles fascifrens (Stal)]

Oat seedlings (Avena sp) were grown in a commercial potting soil incups. When the plants were approximately 10 cm tall they were thinned tothree plants per cup and dipped for 2-3 seconds in 50-50 acetone-watersolutions of the test compounds. When the plants had dried, a clearplastic tube was placed over them and the bottom end pressed into thecup. Ten aster leafhopper adults/nymphs were then placed in each tubeand the tops of the tubes covered with white organdy cloth. Mortalitycounts were made after 48 hours. Test concentrations ranged from 0.05%down to that at which 50% mortality occurred. The LC₅₀ values areexpressed below in Table 3 under the heading "LH" in terms of thepercent of the test compound in the solution.

Maize weevil [Sitophilus zeamais (Motschulsky)]:

Test compounds were diluted in a 50:50 acetone:water solution. Four cornseeds [Zea mays (L.)] which had been immersed in test solutions for 2-3seconds and allowed to dry were placed in containers together with 10adult weevils. The containers were covered and kept at a temperature ofabout 25° C. Mortality was recorded after 48 hours. Test concentrationsranged from 0.01% down to that at which 50% mortality occurred. The LC50values are expressed below in Table 3 under the heading "MW" in terms ofpercent of the test compound in solution.

Rice water weevil [Lissorhoptrus oryzophilus (Kuschel)]:

Test compounds were diluted in acetone. Droplets (1 ul) of testsolutions were applied to the ventral abdomens of ten female adultweevils. The treated weevils were placed in containers with wet cottonballs and rice foliage. The containers were covered and kept at atemperature of about 25° C. Mortality was recorded after 48 hours. Testconcentrations ranged from 0.25 μg/ml or 2.5 μg per weevil down to thatat which 50% mortality occurred. The LC50 values are expressed below inTable 3 under the heading "RWW" in terms of μg of test compound perweevil.

                                      TABLE 3                                     __________________________________________________________________________    (LC.sub.50)                                                                   Cmpd.                                                                             HF          TBW, %                             RWW                        No. μg BBA % C     E    BAW % CL %   LH %  MW % μg                      __________________________________________________________________________     1  4.8   0.0003                                                                              0.06  0.05 0.009 0.005  >0.05 >0.01                                                                              --                          2  4.5   0.0003                                                                              0.0009                                                                              0.04 0.01  0.006  0.0003                                                                              --   --                          3  50    0.003 0.009 >0.1 0.015 0.012  >0.05 >0.01                                                                              --                          4  100   >0.05 0.05  >0.1 0.04  0.007  >0.05 --   --                          5  21    0.001 0.008 0.05 0.025 0.005  >0.05 >0.01                                                                              --                          6  17    0.001 --    0.015                                                                              --    0.02   >0.05 >0.01                                                                              --                          7  8     0.0003                                                                              --    0.009                                                                              0.006 0.006  0.0002                                                                              --   --                          8  50    0.03  --    >0.1 --    0.01   --    >0.01                                                                              --                          9  14    0.001 0.0008                                                                              0.02 0.0005                                                                              0.001  0.0003                                                                              >0.01                                                                              --                          10 > 100 0.05  --    >0.1 --    0.01   >0.05 --   --                          11 6     0.01  --    >0.1 --    0.025  >0.05 >0.01                                                                              --                          12 >100  >0.05 --    >0.1 --    0.008  --    --   --                          13 >100  0.003 --    >0.1 --    0.014  >0.05 >0.01                                                                              --                          14 40    0.0003                                                                              --    --   0.005 0.004  0.001 0.01 --                          15 >100  >0.05 --    >0.1 --    0.025  --    --   --                          16 20    0.0004                                                                              --    0.04 --    0.004  0.0005                                                                              --   --                          17 75    0.03  --    >0.1 --    0.03   >0.05 >0.01                                                                              --                          18 >100  0.003 --    0.09 --    0.008  --    --   --                          19 >100  0.05  --    >0.1 --    <0.1   --    --   --                          20 64    0.0006                                                                              --    <0.1 --    0.0025 0.003 --   --                          21 7     >0.1  --    >0.1 --    0.02   >0.05 >0.01                                                                              --                          22 15    0.01  --    0.08 --    0.004  --    --   --                          23 5     0.001 --    0.017                                                                              0.001 0.0005 --    --   --                          24 25    0.01  --    0.1  --    0.005  --    --   --                          25 >100  >0.1  --    >0.1 --    0.01   >0.05 >0.01                                                                              --                          26 >100  --    --    >0.1 --    0.007  --    --   --                          27 >100  --    --    >0.1 --    0.04   --    --   --                          28 >100  --    --    >0.1 --    0.009  --    --   --                          29 5     0.001 0.001 0.01 0.003 0.002  0.003 >0.01                                                                              --                          30 >100  >0.05 0.01  >0.1 --    0.003  >0.05 >0.01                                                                              --                          31 >100  0.05  0.01  >0.1 0.08  0.05   >0.05 >0.01                                                                              --                          32 37    0.003 0.006 0.1  0.03  0.003  >0.05 >0.01                                                                              --                          33 17    0.003 0.0025                                                                              >0.1 0.02  0.01   >0.05 > 0.01                                                                             --                          34 >100  >0.05 0.01  >0.1 0.015 0.015  --    --   --                          35 15    --    --    0.03 --    0.008  >0.05 >0.01                                                                              --                          36 20    --    --    >0.1 --    0.024  --    --   --                          37 21    --    0.0005                                                                              0.014                                                                              --    0.0004 0.002 0.009                                                                              --                          38 33    --    --    0.05 --    0.006  --    --   --                          39 >100  --    --    >0.1 --    0.0023 --    --   --                          40 36    --    --    0.08 --    0.0025 --    --   --                          41 4.5   0.001 0.0035                                                                              0.04 --    0.015  --    --   --                          42 45    >0.05 >0.1  >0.1 >0.1  >0.1   >0.05 >0.01                                                                              --                          43 7     0.001 --    0.05 --    0.018  >0.05 >0.01                                                                              --                          44 3     0.0006                                                                              <0.1  0.06 --    --     --    --   --                          45 30    0.03  0.01  0.08 0.1   0.03   >0.05 --   --                          46 7     0.003 --    0.016                                                                              0.006 0.003  0.002 --   --                          47 10    0.001 0.002 0.06 0.002 0.002  0.0003                                                                              --   --                          48 >100  >0.05 --    >0.05                                                                              --    0.03   --    --   --                          49 >100  0.05  --    >0.05                                                                              --    0.007  >0.05 --   --                          50 43    0.01  --    >0.05                                                                              --    0.02   >0.05 >0.01                                                                              --                          51 25    0.01  0.0025                                                                              0.067                                                                              --    0.001  0.001 --   --                          52 8     0.001 0.004 >0.05                                                                              0.01  0.0025 0.001 --   --                          53 2     0.001 0.0025                                                                              0.02 0.003 0.0005 --    --   --                          54 3.5   0.001 0.001 0.017                                                                              0.004 0.0003 0.00015                                                                             --   --                          55 >100  0.003 0.004 0.06 0.006 0.0017 0.0005                                                                              --   >2.5                        56 91    0.03  --    >0.05                                                                              --    0.01   --    --   --                          57 >100  0.03  --    0.1  --    0.004  0.0005                                                                              --   --                          58 16    0.003 --    0.06 --    0.002  --    --   --                          59 25    --    --    >0.1 --    0.02   --    --   --                          60 8     --    0.0009                                                                              0.017                                                                              --    0.001  0.002 0.0075                                                                             --                          61 29    0.001 0.03  0.03 0.002 0.001  >0.05 >0.01                                                                              --                          62 20    0.001 0.0015                                                                              0.025                                                                              0.02  0.005  >0.05 >0.01                                                                              --                          63 30    0.0003                                                                              0.001 0.05 0.005 0.005  0.0001                                                                              >0.01                                                                              --                          64 11    0.0006                                                                              0.1   0.03 0.0025                                                                              0.0025 >0.05 >0.01                                                                              --                          65 >100  >0.05 0.1   >0.1 >0.1  <0.01  >0.05 --   --                          66 9.7   0.0003                                                                              --    0.06 0.0065                                                                              <0.0025                                                                              0.001 --   >2.5                        67 15    0.0002                                                                              --    0.01 0.006 0.001  0.00027                                                                             --   --                          68 37    0.0003                                                                              --    0.009                                                                              --    0.006  0.0001                                                                              >0.01                                                                              0.15                        69 >100  >0.05 --    >0.1 --    0.09   >0.05 --   --                          70 <100  <0.05 --    0.01 --    <0.1   >0.05 --   --                          71 50    0.001 0.0008                                                                              0.065                                                                              0.0004                                                                              0.0006 0.002 --   --                          72 >100  >0.05 --    >0.1 --    0.08   >0.05 >0.01                                                                              --                          73 25    0.003 0.005 0.025                                                                              --    0.004  --    --   --                          74 25    0.001 0.0025                                                                              0.025                                                                              --    0.005  --    --   --                          75 5     0.0006                                                                              0.0075                                                                              0.01 --    0.0025 0.0008                                                                              --   --                          76 20    0.003 --    0.05 --    0.002  --    --   --                          77 10    0.001 0.0004                                                                              0.03 0.004 0.0005 0.0002                                                                              >0.01                                                                              --                          78 >100  0.03  --    >0.1 --    0.0025 --    --   --                          79 6     0.03  --    0.05 --    0.003  --    --   --                          80 4.5   0.00025                                                                             0.00075                                                                             0.005                                                                              0.0018                                                                              0.0003 0.0001                                                                              --   --                          81 4     0.001 0.0009                                                                              0.007                                                                              0.003 0.0006 0.0003                                                                              0.005                                                                              >0.5                        82 2.5   0.00021                                                                             0.0008                                                                              0.006                                                                              0.0025                                                                              0.00018                                                                              0.0001                                                                              --   0.086                       83 >100  0.05  --    >0.1 --    0.007  >0.05 --   --                          84 93    0.03  --    0.1  --    0.006  --    --   --                           85                                                                              7     0.0017                                                                              --    >0.1 --    0.004  0.003 >0.01                                                                              >2.5                        86 65    <0.05 --    >0.1 --    0.013  --    --   --                          87 5     0.001 --    0.03 --    0.004  --    --   --                          88 >100  >0.05 --    >0.1 --    0.018  --    >0.01                                                                              --                          89 5     0.003 0.0005                                                                              0.04 0.009 0.00003                                                                              0.001 0.005                                                                              >2.5                        90 >100  0.0003                                                                              --    0.016                                                                              --    >0.1   0.001 --   --                          91 37    0.001 --    >0.01                                                                              --    0.002  0.003 --   --                          92 >100  >0.05 --    >0.1 --    0.015  >0.05 --   --                          93 64    0.003 --    >0.1 --    0.005  --    --   --                          94 44    0.001 --    0.075                                                                              --    0.0045 --    --   --                          95 10    0.001 0.004 0.025                                                                              --    0.0025 --    --   --                          96 35    0.002 0.0025                                                                              0.025                                                                              --    0.003  --    --   --                          97 10    0.001 0.004 0.04 0.01  0.002  --    --   --                          98 >100  >0.05 --    0.1  --    0.016  >0.05 --   --                          99 >100  >0.05 --    >0.1 --    0.016  --    --   --                         100 100   >0.05 --    >0.1 --    0.05   --    --   --                         101 81    0.002 --    >0.1 --    0.0045 0.0008                                                                              --   --                         102 >100  0.05  --    >0.1 --    0.075  >0.05 --   --                         103 >100  0.001 --    >0.1 --    0.015  --    --   --                         104 >100  0.003 --    >0.1 --    0.004  --    --   --                         105 >100  0.05  --    >0.1 --    0.018  --    --   --                         106 >100  0.01  --    >0.1 --    0.014  --    --   --                         107 >100  0.01  --    >0.1 --    0.007  --    --   --                         108 44    0.01  --    >0.1 --    0.002  >0.01 --   --                         109 >100  > 0.05                                                                              --    >0.1 --    0.002  --    --   --                         110 26    --    --    0.04 --    0.007  --    --   --                         111 >100  0.003 --    >0.1 --    0.1    --    --   --                         112 >100  0.05  --    >0.1 --    0.025  >0.05 >0.01                                                                              --                         113 15    --    --    0.1  --    0.005  --    --   >2.5                       114 92    --    --    --   --    <0.1   --    --   --                         115 10    --    --    0.075                                                                              --    0.0012 --    --   --                         116 15    --    --    0.05 --    0.00025                                                                              --    >0.01                                                                              --                         117 55    >0.05 --    >0.1 --    0.006  0.0003                                                                              >0.01                                                                              --                         118 18    --    --    >0.1 --    0.0013 --    --   --                         119 27    >0.05 --    0.048                                                                              --    0.0007 0.0008                                                                              >0.01                                                                              --                         120 14    0.0006                                                                              0.0025                                                                              0.04 --    0.00015                                                                              0.0003                                                                              >0.01                                                                              --                         121 >100  --    --    >0.1 --    0.1    --    --   --                         122 37    >0.05 --    0.05 0.01  0.0007 >0.05 >0.01                                                                              --                         123 >100  --    --    >0.1 --    0.012  --    --   --                         124 17    >0.05 --    >0.1 --    0.01   >0.05 >0.01                                                                              --                         125 12    0.05  --    0.025                                                                              --    0.0007 >0.05 >0.01                                                                              >2.5                       126 >100  --    --    >0.1 --    0.08   --    --   --                         127 58    0.001 --    0.04 --    0.01   --    --   --                         128 4.5   0.001 --    0.037                                                                              --    0.005  0.003 >0.01                                                                              --                         129 >100  0.03  --    >0.1 --    0.005  0.01  --   --                         130 >100  0.05  --    >0.1 --    0.005  --    --   --                         131 17    0.003 --    >0.1 --    0.0045 0.005 --   --                         132 65    0.0025                                                                              --    >0.1 --    0.025  >0.05 >0.01                                                                              --                         133 66    0.003 --    0.1  --    0.005  --    --   --                         134 >100  >0.05 --    >0.1 --    0.015  --    --   --                         135 >100  >0.05 --    >0.1 --    0.004  >0.05 --   --                         136 9     0.002 --    0.08 --    0.004  --    --   --                         137 18    0.03  --    0.04 --    0.003  0.008 --   --                         138 19    0.003 0.015 0.08 --    0.005  >0.05 >0.01                                                                              --                         139 4.2   0.001 0.005 0.05 0.007 0.015  --    --   --                         140 >100  0.05  >0.1  >0.1 --    <0.1   --    --   --                         141 35    0.006 --    >0.1 --    <0.1   --    --   --                         142 15    0.001 --    0.1  --    0.005  >0.05 >0.01                                                                              --                         143 10    0.002 --    <0.1 --    0.002  0.006 >0.01                                                                              --                         144 100   0.003 0.006 0.05 >0.01 0.002  0.0006                                                                              >0.01                                                                              --                         145 >100  >0.05 0.05  >0.1 --    0.05   >0.05 --   --                         146 40    0.05  0.025 >0.1 --    0.017  --    --   --                         147 10    0.03  0.0075                                                                              >0.1 --    0.01   --    --   --                         148 18    0.0003                                                                              --    0.025                                                                              --    0.0025 --    --   --                         149 17    0.001 --    0.05 --    0.007  --    --   --                         150 89    0.03  --    >0.1 --    0.01   --    --   --                         151 38    0.006 --    >0.1 --    0.009  >0.05 >0.01                                                                              --                         152 >100  0.01  --    >0.1 --    0.009  --    --   --                         153 >100  0.003 --    0.1  --    0.004  0.0005                                                                              >0.01                                                                              --                         154 25    0.002 --    0.1  --    0.004  >0.05 --   --                         155 9     0.001 --    0.06 --    0.004  >0.05 >0.01                                                                              --                         156 10    0.001 --    0.05 --    0.004  >0.05 >0.01                                                                              --                         157 25    0.002 --    >0.1 --    0.009  --    --   --                         158 9     0.0015                                                                              --    0.1  --    0.003  --    --   --                         159 25    0.001 --    0.08 --    0.001  0.0025                                                                              --   --                         160 7     0.003 --    0.09 --    0.005  0.05  >0.01                                                                              --                         161 15    0.0006                                                                              --    0.07 --    0.0014 0.002 --   --                         162 >100  >0.05 --    >0.1 --    0.035  >0.05 --   --                         163 >100  >0.05 --    >0.1 --    0.004  --    >0.01                                                                              --                         164 >100  >0.05 --    >0.1 --    0.005  --    --   --                         165 >100  >0.05 --    >0.1 --    0.007  --    --   --                         166 22    0.001 --    >0.1 --    0.009  --    --   --                         167 >100  >0.05 --    >0.1 --    0.02   --    --   --                         168 >100  >0.05 --    >0.1 --    0.1    --    --   --                         169 10    0.003 --    >0.1 --    0.009  --    --   --                         170 37    --    --    >0.1 --    0.1    --    --   --                         171 80    --    --    >0.1 --    0.01   --    --   --                         172 5     >0.05 --    0.04 --    0.002  >0.05 >0.01                                                                              --                         173 18    >0.05 >0.1  >0.1 >0.1  0.02   --    --   --                         174 17    0.05  --    >0.1 0.1   0.03   --    --   --                         175 >100  >0.05 --    >0.1 --    0.018  --    --   --                         176 1.8   0.0006                                                                              0.002 0.05 0.0035                                                                              0.0005 >0.05 0.009                                                                              --                         177 13    0.01  --    >0.1 --    0.002  >0.05 0.01 --                         178 6     0.05  --    >0.1 --    0.004  >0.05 >0.01                                                                              --                         179 13    0.003 --    >0.1 --    0.004  0.005 >0.01                                                                              --                         180 2     0.0003                                                                              0.003 0.03 0.005 0.0004 0.0015                                                                              0.008                                                                              >2.5                       181 25    --    0.001 0.01 0.001 0.0005 --    0.005                                                                              >2.5                       182 28    --    --    0.04 --    0.0006 --    --   --                         183 10    --    --    0.075                                                                              --    0.00075                                                                              --    --   --                         184 61    --    --    >0.1 --    0.024  --    --   --                         185 13    --    --    0.075                                                                              --    0.0006 --    --   --                         186 >100  >0.05 --    >0.1 --    0.008  >0.05 >0.01                                                                              --                         187 15    0.001 --    >0.1 --    0.0025 0.0025                                                                              --   --                         188 12    --    --    >0.1 --    0.002  >0.05 --   --                         189 17    --    --    0.07 --    0.00027                                                                              0.002 >0.01                                                                              --                         190 7.5   --    --    0.023                                                                              --    0.0004 --    --   --                         191 29    0.001 --    0.04 --    0.00023                                                                              >0.05 0.004                                                                              >2.5                       192 25    --    --    0.07 --    0.0012 --    --   --                         193 100   --    --    >0.1 --    0.00075                                                                              0.001 >0.01                                                                              --                         194 10    0.001 0.0017                                                                              0.04 --    0.0005 0.0005                                                                              >0.01                                                                              --                         195 >100  --    --    >0.1 --    0.002  --    --   --                         196 17    --    0.001 >0.1 --    0.0006 >0.05 >0.01                                                                              --                         197 >100  --    --    0.05 --    0.0004 --    --   --                         198 52    --    --    >0.1 --    0.0005 0.05  0.003                                                                              >2.5                       199 8     --    0.003 >0.1 --    0.0006 --    >0.01                                                                              --                         200 7.5   --    --    0.1  --    0.00075                                                                              --    --   --                         201 15    --    --    >0.1 --    0.004  --    --   --                         202 18    0.003 0.0007                                                                              >0.1 --    0.00024                                                                              0.0003                                                                              >0.01                                                                              --                         203 43    0.006 --    0.06 --    0.0025 --    >0.01                                                                              --                         204 >100  --    0.004 >0.1 --    0.0023 --    >0.01                                                                              --                         205 50    0.03  --    >0.1 --    0.004  --    --   --                         206 50    0.03  --    >0.1 --    0.0017 --    --   --                         207 >100  --    --    >0.1 --    0.008  --    --   --                         208 27    0.05  --    >0.1 --    0.0035 --    --   --                         209 17    0.01  0.005 0.1  --    0.0007 0.001 >0.01                                                                              --                         210 35    0.01  0.0015                                                                              0.045                                                                              --    0.00028                                                                              --    >0.01                                                                              --                         211 61    0.01  --    >0.1 --    0.0017 --    --   --                         212 20    0.05  --    0.045                                                                              --    0.0005 --    --   --                         213 >100  0.01  --    >0.1 --    0.00075                                                                              --    --   --                         214 19    0.01  --    0.04 --    0.0003 --    --   --                         215 75    0.05  --    >0.1 --    0.00075                                                                              --    --   --                         216 2     0.00025                                                                             0.00018                                                                             0.005                                                                              0.0007                                                                              0.000007                                                                             0.00025                                                                             0.0017                                                                             0.067                      217 8     0.001 --    0.015                                                                              --    0.00006                                                                              >0.05 0.0084                                                                             --                         218 25    0.003 --    0.025                                                                              --    0.0003 --    --   --                         219 50    0.003 0.004 0.027                                                                              --    0.00025                                                                              --    >0.01                                                                              --                         220 85    0.03  --    >0.1 --    0.007  --    --   --                         221 62    0.01  --    >0.1 --    0.0027 --    --   --                         222 32    0.01  --    >0.1 --    0.0015 --    --   --                         223 43    0.003 --    >0.1 --    0.008  --    --   --                         224 >100  0.05  --    >0.1 --    0.001  --    --   --                         225 >100  0.006 --    >0.1 --    0.0025 >0.05 --   --                         226 16    0.01  0.001 0.1  --    0.0005 0.002 0.009                                                                              --                         227 10    0.01  --    0.1  --    0.0015 --    --   --                         228 >100  0.01  --    >0.1 --    0.0025 >0.05 --   --                         229 20    0.006 --    >0.1 --    0.0005 --    --   --                         230 36    0.01  --    0.1  --    0.0004 --    0.038                                                                              >2.5                       231 >100  0.01  --    >0.1 --    0.003  --    --   --                         232 >100  >0.05 --    >0.1 --    0.004  --    --   --                         233 10    0.01  --    0.09 --    0.0017 --    --   --                         234 38    0.003 0.0013                                                                              0.09 --    0.00045                                                                              0.003 >0.01                                                                              --                         235 >100  0.01  --    >0.1 --    0.004  --    --   --                         236 7     0.003 --    0.06 --    0.0018 --    --   --                         237 50    0.01  --    0.075                                                                              --    0.0006 --    --   --                         238 25    0.003 0.0004                                                                              0.05 --    0.0002 >0.05 >0.01                                                                              --                         239 14    0.001 0.0005                                                                              0.025                                                                              0.005 0.00015                                                                              0.002 0.006                                                                              >2.5                       240 14    0.001 --    0.04 --    0.0003 >0.05 >0.01                                                                              --                         241 >100  <0.05 --    >0.1 --    0.0004 --    --   --                         242 <100  <0.05 --    >0.1 --    0.00025                                                                              >0.05 --   --                         243 9     0.01  --    >0.1 --    0.005  --    --   --                         244 14    0.0006                                                                              0.00025                                                                             >0.1 0.002 0.00004                                                                              --    0.0025                                                                             0.09                       245 20    0.0003                                                                              0.0015                                                                              0.016                                                                              0.001 0.0035 --    0.006                                                                              >2.5                       246 60    >0.05 --    >0.1 --    0.004  --    --   --                         247 >100  >0.05 --    >0.1 --    0.009  --    --   --                         248 40    >0.05 --    >0.1 --    0.02   --    --   --                         249 36    0.0003                                                                              --    0.035                                                                              --    0.0025 --    --   --                         250 38    0.0006                                                                              --    0.038                                                                              --    0.004  --    --   --                         251 25    0.001 --    0.06 --    0.0005 --    --   --                         252 34    0.002 --    0.04 --    0.0035 --    --   --                         253 10    0.002 0.0005                                                                              >0.1 --    0.00013                                                                              0.003 >0.01                                                                              --                         254 6     0.001 --    0.026                                                                              --    0.001  --    --   >2.5                       255 16    0.003 --    0.075                                                                              --    0.00017                                                                              0.0005                                                                              >0.01                                                                              --                         256 >100  0.03  --    0.1  --    0.007  >0.05 >0.01                                                                              --                         257 >100  0.05  --    >0.1 --    0.008  >0.05 --   --                         258 >100  0.01  --    >0.1 --    0.003  >0.05 --   --                         259 15    0.006 --    0.05 --    0.0003 >0.05 >0.01                                                                              --                         260 22    0.006 --    >0.1 --    0.00075                                                                              --    --   --                         261 24    0.002 --    0.05 --    0.001  --    --   --                         262 26    0.03  --    >0.1 --    0.0004 --    0.005                                                                              >2.5                       263 >100  >0.05 --    >0.1 --    0.05   --    --   --                         264 >100  >0.05 --    >0.1 --    0.03   --    --   --                         265 10    >0.05 --    0.07 --    0.00025                                                                              --    --   --                         266 10    >0.05 0.0007                                                                              0.06 --    0.00016                                                                              --    --   --                         267 8.4   0.0003                                                                              0.0003                                                                              0.015                                                                              0.0012                                                                              0.00008                                                                              0.002 0.0027                                                                             0.11                       268 4     >0.05 0.0005                                                                              0.023                                                                              0.001 0.000025                                                                             0.0005                                                                              >0.01                                                                              --                         269 25    >0.05 0.001 0.04 0.0024                                                                              0.0003 0.003 >0.01                                                                              >2.5                       270 12    >0.05 >0.0015                                                                             >0.01                                                                              0.005 0.00025                                                                              0.003 >0.01                                                                              --                         271 27    >0.05 --    0.1  --    0.0004 >0.05 >0.01                                                                              --                         272 >100  >0.05 --    >0.1 --    0.0024 --    --   --                         273 7     0.0003                                                                              0.00025                                                                             0.015                                                                              0.0017                                                                              0.000018                                                                             0.0003                                                                              0.004                                                                              >2.5                       274 >100  >0.05 --    >0.1 --    0.1    --    --   --                         275 21    --    --    0.045                                                                              --    0.00012                                                                              --    --   --                         276 39    --    --    0.1  --    0.002  --    --   --                         277 4     0.0008                                                                              0.0005                                                                              0.013                                                                              0.005 0.00001                                                                              0.0003                                                                              >0.01                                                                              0.065                      278 3     0.0005                                                                              0.00026                                                                             0.008                                                                              0.0012                                                                              0.00002                                                                              0.0003                                                                              0.0063                                                                             0.085                      279 4     0.0005                                                                              0.007 0.016                                                                              0.0025                                                                              0.00008                                                                              0.0003                                                                              >0.01                                                                              --                         280 >100  --    --    >0.1 --    0.024  --    --   --                         281 5     0.0003                                                                              0.00025                                                                             0.006                                                                              0.0027                                                                              0.00002                                                                              --    0.005                                                                              >2.5                       282 16    --    0.0007                                                                              0.02 0.0025                                                                              0.00007                                                                              --    0.008                                                                              --                         283 23    --    0.0009                                                                              0.016                                                                              0.0013                                                                              0.00009                                                                              --    >0.01                                                                              --                         284 39    0.0003                                                                              0.0002                                                                              --   0.0025                                                                              0.00005                                                                              0.0003                                                                              0.0075                                                                             --                         285 36    --    0.00017                                                                             0.005                                                                              0.0006                                                                              0.000075                                                                             --    0.005                                                                              0.13                       286 34    0.0003                                                                              0.00017                                                                             0.005                                                                              0.0004                                                                              0.000024                                                                             0.0006                                                                              0.0039                                                                             0.09                       287 >100  --    --    >0.1 --    0.0025 --    --   --                         288 >100  --    --    >0.1 --    0.0015 --    --   --                         289 10    0.0003                                                                              --    0.006                                                                              --    0.00007                                                                              0.0003                                                                              >0.01                                                                              0.082                      290 >100  --    --    >0.1 --    0.017  --    --   --                         291 >100  --    --    >0.1 --    0.004  --    --   --                         292 41    --    --    0.05 --    0.00075                                                                              --    >0.01                                                                              --                         293 19    >0.05 --    >0.1 --    0.0045 >0.05 >0.01                                                                              --                         294 >100  --    --    >0.1 --    0.017  --    >0.01                                                                              --                         295 7.8   0.0003                                                                              0.0005                                                                              0.01 --    0.00004                                                                              0.0001                                                                              0.0053                                                                             >2.5                       296 38    0.0003                                                                              0.00045                                                                             0.025                                                                              --    0.00025                                                                              0.0003                                                                              --   0.14                       297 23    --    0.00075                                                                             0.025                                                                              --    0.00027                                                                              0.0001                                                                              0.0071                                                                             --                         298 13    --    0.0008                                                                              0.015                                                                              --    0.0001 0.0001                                                                              0.008                                                                              >2.5                       299 8     --    --    0.017                                                                              --    0.0005 --    >0.01                                                                              --                         300 14    0.0003                                                                              0.001 0.024                                                                              --    0.0003 0.00002                                                                             0.01 0.075                      301 >100  --    --    >0.1 --    0.008  --    >0.01                                                                              --                         302 15    --    --    >0.1 --    0.003  --    >0.01                                                                              --                         303 >100  --    --    >0.1 --    0.0015 0.0005                                                                              --   --                         304 >100  --    --    >0.1 --    0.0024 --    >0.01                                                                              --                         305 >100  --    --    >0.1 --    0.048  --    --   --                         306 >100  --    --    0.1  --    0.005  --    >0.01                                                                              --                         307 >100  --    --    0.08 --    0.002  --    >0.01                                                                              --                         308 >100  --    --    >0.1 --    0.009  --    --   --                         309 >100  --    --    0.07 --    0.00017                                                                              --    --   --                         310 4.5   0.0006                                                                              --    0.015                                                                              --    0.00006                                                                              --    --   >2.5                       311 22    --    --    0.1  --    0.0017 --    --   --                         312 >100  --    --    >0.1 --    0.006  --    --   --                         313 >100  --    --    0.013                                                                              --    0.00025                                                                              --    --   --                         314 21    --    --    0.012                                                                              --    0.00005                                                                              --    --   0.11                       315 >100  >0.05 --    >0.1 --    0.002  >0.05 >0.01                                                                              --                         316 100   >0.05 --    >0.1 --    0.0015 >0.05 >0.01                                                                              --                         317 >100  --    --    0.03 --    0.0045 --    --   --                         318 19    --    --    >0.1 --    0.0007 --    --   --                         319 44    --    --    >0.1 --    0.0007 --    --   --                         320 >100  --    --    >0.1 --    0.0075 --    --   --                         321 >100  --    --    >0.1 --    0.05   --    --   --                         322 >100  --    --    >0.1 --    0.007  --    --   --                         323 >100  >0.05 0.00065                                                                             0.045                                                                              0.0025                                                                              0.0006 0.05  0.0075                                                                             0.16                       324 >100  0.0003                                                                              0.0004                                                                              0.025                                                                              0.0024                                                                              0.00014                                                                              --    --   0.06                       325 5     0.0001                                                                              0.0006                                                                              0.037                                                                              0.0025                                                                              0.00012                                                                              --    --   >2.5                       326 25    >0.05 0.0005                                                                              0.03 0.004 0.00015                                                                              --    --   --                         327 >100  >0.05 --    >0.1 --    0.005  --    --   --                         328 >100  >0.05 --    >0.1 --    0.03   --    --   --                         329 7     >0.05 --    >0.1 --    0.033  --    --   --                         330 5     0.0001                                                                              0.00035                                                                             0.037                                                                              --    0.00012                                                                              <0.05 0.001                                                                              0.06                       331 20    >0.05 0.0004                                                                              0.04 0.002 0.0002 --    --   >2.5                       332 7     >0.05 0.00075                                                                             0.015                                                                              0.0012                                                                              0.00045                                                                              --    --   --                         333 15    0.001 0.00075                                                                             0.025                                                                              >0.1  0.00024                                                                              --    >0.01                                                                              --                         334 9     0.0006                                                                              --    0.013                                                                              --    0.0007 --    >0.01                                                                              --                         335 34    0.0008                                                                              0.00025                                                                             0.05 >0.1  0.00027                                                                              --    >0.01                                                                              --                         336 3.6   0.0003                                                                              0.0005                                                                              0.02 0.001 0.00017                                                                              --    0.0091                                                                             >2.5                       337 21    0.0003                                                                              0.0005                                                                              0.008                                                                              0.0005                                                                              0.0007 --    0.0053                                                                             0.067                      338 26    0.0003                                                                              0.00037                                                                             0.01 --    0.000065                                                                             --    0.0053                                                                             0.044                      339 >100  0.03  --    >0.1 --    0.017  --    >0.01                                                                              --                         340 34    0.001 --    0.04 --    0.00037                                                                              --    0.0069                                                                             --                         341 4     0.0005                                                                              --    0.023                                                                              --    0.0005 --    >0.01                                                                              --                         342 4.1   0.0006                                                                              --    0.04 --    0.0008 --    >0.01                                                                              --                         343 40    0.002 0.00025                                                                             >0.1 >0.1  0.00027                                                                              --    >0.01                                                                              --                         344 >100  0.008 --    >0.1 --    0.024  --    >0.01                                                                              --                         345 >100  0.006 --    >0.1 --    0.018  --    >0.01                                                                              --                         346 7.2   0.0008                                                                              0.0002                                                                              >0.1 >0.1  >0.1   0.05  >0.01                                                                              --                         347 30    0.0002                                                                              0.0001                                                                              >0.1 0.00075                                                                             0.000075                                                                             0.0002                                                                              >0.01                                                                              --                         348 8     0.001 0.00075                                                                             >0.1 >0.1  0.0002 0.05  >0.01                                                                              --                         349 4.9   >0.05 0.0004                                                                              >0.1 >0.1  0.00007                                                                              --    >0.01                                                                              >2.5                       350 >100  >0.05 --    >0.1 --    0.0045 >0.05 >0.01                                                                              --                         351 26    0.001 --    >0.1 --    0.0007 >0.05 >0.01                                                                              --                         352 4.6   0.0003                                                                              0.0004                                                                              >0.1 >0.1  0.000065                                                                             0.0004                                                                              0.0075                                                                             >2.5                       353 <100  0.001 --    >0.1 --    >0.1   >0.05 >0.01                                                                              --                         354 <100  0.001 --    0.018                                                                              --    >0.1   <0.05 0.0068                                                                             --                         355 <100  0.0006                                                                              --    >0.1 --    >0.1   <0.05 >0.01                                                                              --                         356 <100  0.001 --    0.025                                                                              --    >0.1   <0.05 >0.01                                                                              --                         357 <100  0.0003                                                                              --    >0.1 --    >0.1   <0.05 0.01 --                         358 <100  0.0003                                                                              --    >0.1 --    >0.1   <0.05 >0.01                                                                              --                         359 <100  0.0006                                                                              --    0.023                                                                              --    >0.1   0.05  >0.01                                                                              --                         360 <100  0.0006                                                                              --    >0.1 --    0.006  <0.05 >0.01                                                                              --                         361 <100  0.0003                                                                              --    0.04 --    0.001  <0.05 >0.01                                                                              --                         362 <100  0.005 --    >0.1 --    >0.1   >0.05 >0.01                                                                              --                         363 <100  0.005 --    >0.1 --    >0.1   >0.05 >0.01                                                                              --                         364 <100  0.001 --    0.025                                                                              --    0.00045                                                                              <0.05 >0.01                                                                              --                         365 >100  0.003 --    0.038                                                                              --    0.00025                                                                              <0.05 >0.01                                                                              --                         366 <100  0.0006                                                                              --    0.012                                                                              --    0.0007 0.05  >0.01                                                                              --                         367 >100  >0.05 --    >0.1 --    <0.1   >0.05 >0.01                                                                              --                         368 <100  0.001 --    0.04 --    0.002  --    >0.01                                                                              --                         369 >100  0.0003                                                                              --    >0.1 --    0.0016 --    >0.01                                                                              >2.5                       370 <100  0.0002                                                                              --    0.02 --    0.00034                                                                              --    >0.01                                                                              >2.5                       371 <100  0.0004                                                                              --    >0.1 --    0.0022 --    >0.01                                                                              --                         372 >100  0.001 --    >0.1 --    >0.1   --    >0.01                                                                              --                         373 <100  0.001 --    >0.1 --    >0.1   --    >0.01                                                                              --                         374 <100  0.0008                                                                              --    0.02 --    0.00058                                                                              --    >0.01                                                                              --                         375 7.9   0.0006                                                                              --    0.04 --    >0.1   --    >0.01                                                                              >2.5                       376 17    0.0003                                                                              --    0.02 --    0.00037                                                                              --    0.0061                                                                             0.1                        377 <100  0.001 --    >0.1 --    0.00062                                                                              --    >0.01                                                                              >2.5                       378 <100  0.0008                                                                              --    0.02 --    0.00034                                                                              --    >0.01                                                                              >2.5                       379 <100  0.0006                                                                              --    0.02 --    0.00075                                                                              --    >0.01                                                                              --                         380 >100  0.004 --    >0.1 --    >0.1   --    >0.01                                                                              >2.5                       381 <100  0.002 --    0.018                                                                              --    0.00092                                                                              --    >0.01                                                                              >2.5                       382 <100  0.0003                                                                              --    0.027                                                                              --    0.00029                                                                              --    >0.01                                                                              >2.5                       383 <100  0.0006                                                                              --    0.038                                                                              --    0.00029                                                                              --    >0.01                                                                              --                         384 <100  0.0008                                                                              --    0.025                                                                              --    >0.1   --    >0.01                                                                              --                         385 <100  >0.05 --    >0.1 --    >0.1   --    >0.01                                                                              --                         386 <100  0.002 --    >0.1 --    0.0012 --    >0.01                                                                              --                         387 <100  0.0006                                                                              --    0.05 --    0.0012 --    >0.01                                                                              >2.5                       388 <100  0.0006                                                                              --    >0.1 --    0.0012 --    >0.01                                                                              --                         389 <100  0.003 --    >0.1 --    0.00069                                                                              --    >0.01                                                                              --                         390 <100  0.0006                                                                              --    0.045                                                                              --    0.0021 --    >0.01                                                                              --                         391 <100  0.0006                                                                              --    0.035                                                                              --    0.00029                                                                              --    >0.01                                                                              >2.5                       392 <100  0.001 --    0.039                                                                              --    0.00034                                                                              --    >0.01                                                                              --                         393 <100  >0.05 --    >0.1 --    0.00037                                                                              --    >0.01                                                                              --                         394 <100  0.002 --    0.05 --    0.00025                                                                              --    >0.01                                                                              --                         395 8.6   0.0001                                                                              --    0.018                                                                              --    <0.1   --    0.004                                                                              --                         396 <100  0.0002                                                                              --    <0.1 --    0.0017 --    >0.01                                                                              --                         397 <100  0.002 --    <0.1 --    0.0019 --    >0.01                                                                              --                         398 <100  0.002 --    <0.1 --    <0.1   --    >0.01                                                                              --                         399 <100  0.0003                                                                              --    0.025                                                                              --    0.0012 --    >0.01                                                                              --                         400 <100  0.0003                                                                              --    0.025                                                                              --    0.0007 --    >0.01                                                                              --                         401 <100  0.0006                                                                              --    0.04 --    0.0017 --    >0.01                                                                              --                         402 <100  0.0006                                                                              --    >0.1 --    >0.1   --    >0.01                                                                              --                         403 <100  0.001 --    >0.1 --    >0.1   --    >0.01                                                                              --                         404 <100  0.002 --    0.025                                                                              --    >0.1   --    >0.01                                                                              --                         405 <100  0.0025                                                                              --    >0.1 --    >0.1   --    >0.01                                                                              --                         406 <100  0.001 --    <0.1 --    >0.1   --    >0.01                                                                              --                         407 >100  0.0007                                                                              --    0.05 --    >0.1   --    >0.01                                                                              --                         408 <100  0.0005                                                                              --    0.02 --    0.0015 --    >0.01                                                                              --                         409 <100  0.0005                                                                              --    0.025                                                                              --    0.0017 --    >0.01                                                                              --                         410 <100  0.0025                                                                              --    >0.1 --    >0.1   --    >0.01                                                                              --                         411 <100  >0.05 --    >0.1 --    >0.1   --    >0.01                                                                              --                         412 <100  0.0032                                                                              --    >0.1 --    >0.1   --    >0.01                                                                              --                         413 <100  >0.05 --    0.04 --    0.0007 --    >0.01                                                                              --                         414 < 100 >0.05 --    >0.1 --    0.0024 --    >0.01                                                                              --                         415 <100  0.0007                                                                              --    0.035                                                                              --    0.00075                                                                              --    >0.01                                                                              --                         416 <100  0.0035                                                                              --    0.018                                                                              --    0.00027                                                                              --    >0.01                                                                              --                         417 <100  0.004 --    0.04 --    0.0008 --    >0.01                                                                              --                         *418                                                                              >100  >0.05 --    >0.1 --    >0.1   --    >0.01                                                                              --                         *419                                                                              >100  >0.05 --    >0.1 --    >0.1   --    >0.01                                                                              --                         420 >100  0.004 --    0.05 --    0.00075                                                                              --    >0.01                                                                              --                         421 >100  >0.05 --    <0.1 --    0.002  --    >0.01                                                                              --                         422 <100  >0.05 --    0.05 --    0.00075                                                                              --    >0.01                                                                              --                         423 >100  >0.05 --    >0.1 --    0.002  --    >0.01                                                                              --                         424 >100  0.002 --    0.035                                                                              --    0.00038                                                                              --    >0.01                                                                              --                         425 >100  0.0035                                                                              --    >0.1 --    0.00075                                                                              --    >0.01                                                                              --                         426 >100  0.0012                                                                              --    >0.1 --    0.002  --    >0.01                                                                              --                         427 >100  0.05  --    >0.1 --    <0.1   --    >0.01                                                                              --                         428 >100  0.003 --    >0.1 --    0.0017 --    >0.01                                                                              --                         429 >100  0.005 --    <0.1 --    0.0017 --    >0.01                                                                              --                         430 <100  0.0006                                                                              --    0.032                                                                              --    0.001  --    0.004                                                                              --                         431 9.8   0.0003                                                                              --    0.025                                                                              --    0.00017                                                                              --    0.0037                                                                             0.084                      432 <100  0.001 <0.1  0.032                                                                              --    0.0012 --    >0.01                                                                              --                         433 <100  0.0003                                                                              --    0.02 --    0.00017                                                                              --    0.005                                                                              0.078                      434 <100  0.003 --    >0.1 --    0.0017 --    0.009                                                                              --                         435 <100  0.001 --    0.04 --    0.002  --    >0.01                                                                              --                         436 <100  0.0006                                                                              --    <0.1 --    0200075                                                                              --    >0.01                                                                              --                         437 <100  0.0003                                                                              --    0.025                                                                              --    0.00075                                                                              --    >0.01                                                                              --                         438 > 100 0.0003                                                                              --    <0.1 --    0.0009 --    >0.01                                                                              --                         439 >100  0.0003                                                                              --    >0.1 --    0.00045                                                                              --    >0.01                                                                              --                         440 >100  0.0003                                                                              --    <0.1 --    0.002  --    >0.01                                                                              --                         441 <100  0.0003                                                                              --    0.016                                                                              --    0.000025                                                                             --    0.006                                                                              --                         442 <100  0.001 --    0.035                                                                              --    0.0007 --    >0.01                                                                              --                         443 <100  0.0003                                                                              --    0.017                                                                              --    0.00015                                                                              --    <0.01                                                                              --                         444 >100  0.0006                                                                              --    0.023                                                                              --    0.00015                                                                              --    >0.01                                                                              --                         445 <100  0.001 --    >0.1 --    0.00045                                                                              --    >0.01                                                                              --                         446 >100  0.001 --    <0.1 --    0.0008 --    >0.01                                                                              --                         447 33    >0.05 --    >0.1 --    0.0009 --    --   --                         448 16    >0.05 --    0.03 --    0.003  --    --   --                         449 13    --    --    0.025                                                                              --    0.0001 --    0.0075                                                                             --                         450 72    --    0.0001                                                                              0.015                                                                              0.005 0.00016                                                                              --    0.01 --                         451 3.6   0.001 0.00025                                                                             >0.1 --    0.0001 0.0002                                                                              0.0051                                                                             0.065                      452 >100  0.0003                                                                              --    <0.1 --    0.0017 --    >0.01                                                                              0.1                        453 >100  >0.05 --    --   --    0.1    --    --   --                         454 >100  >0.05 --    >0.1 --    0.03   --    --   --                         455 >100  0.01  --    >0.1 --    0.0025 --    --   --                         456 >100  0.01  --    >0.05                                                                              --    0.017  >0.05 >0.01                                                                              --                         457 >100  >0.05 --    >0.05                                                                              --    0.009  >0.05 --   --                         458 100   >0.05 --    >0.05                                                                              --    0.007  --    --   --                         459 >100  >0.05 --    0.1  --    0.008  --    >0.01                                                                              --                         460 >100  >0.05 --    >0.1 --    0.02   --    >0.01                                                                              --                         461 6     0.001 --    0.01 0.0035                                                                              0.00008                                                                              --    0.0075                                                                             >2.5                       462 7     0.001 0.0025                                                                              0.04 --    0.001  0.001 >0.05                                                                              --                         463 8     0.05  --    0.0075                                                                             0.0024                                                                              0.00009                                                                              0.0003                                                                              0.01 --                         464 >100  --    --    >0.1 --    0.08   --    --   --                         465 8     --    --    0.027                                                                              --    0.0017 0.0025                                                                              --   --                         466 13    --    --    >0.1 --    0.0008 >0.05 0.01 --                         467 6     --    --    0.04 --    0.003  --    --   --                         468 50    0.05  --    >0.1 --    >0.1   --    --   --                         469 40    >0.05 --    >0.1 --    0.02   --    --   --                         470 25    >0.05 --    >0.1 --    0.02   --    --   --                         471 <100  0.001 --    0.018                                                                              --    0.00018                                                                              --    >0.01                                                                              --                         472 >100  --    --    >0.1 --    0.0025 --    --   --                         473 >100  --    --    >0.1 --    0.025  --    --   --                         474 8     --    --    >0.1 --    0.0012 --    --   --                         475 > 100 >0.05 --    >0.1 --    0.008  >0.05 >0.01                                                                              --                         476 >100  --    --    >0.1 --    0.015  --    --   --                         477 20    --    --    >0.1 --    0.0003 --    0.0076                                                                             --                         478 15    --    --    >0.1 --    0.0037 --    >0.01                                                                              --                         479 66    >0.05 --    >0.1 --    0.013  >0.05 >0.01                                                                              --                         480 >100  >0.05 --    >0.1 --    0.01   --    --   --                         481 >100  --    --    >0.1 --    0.015  --    --   --                         482 36    --    --    >0.1 --    0.01   --    >0.01                                                                              --                         483 6     --    --    0.05 --    0.001  --    >0.01                                                                              --                         484 16    --    --    >0.1 --    0.003  --    --   --                         485 24    --    --    >0.1 --    >0.1   --    --   --                         486 15    --    --    >0.1 --    >0.1   --    >0.01                                                                              --                         487 >100  --    --    >0.1 --    0.023  --    --   --                         488 >100  --    --    >0.1 --    0.025  --    --   --                         489 >100  --    --    >0.1 --    <0.1   --    --   --                         490 >100  >0.05 --    >0.1 --    0.0045 >0.05 >0.01                                                                              --                         491 9     --    --    0.08 --    0.0028 --    --   --                         492 15    >0.05 --    0.015                                                                              --    0.00028                                                                              >0.05 >0.01                                                                              --                         493 36    --    --    0.05 --    0.0008 --    --   --                         494 34    --    --    >0.1 --    0.003  --    --   --                         495 >100  --    --    0.1  --    0.012  --    --   --                         496 >100  --    --    >0.1 --    0.006  --    --   --                         497 >100  --    --    >0.1 --    0.0075 --    --   --                         498 49    > 0.05                                                                              --    >0.1 --    0.002  --    --   --                         499 63    >0.05 --    >0.1 --    0.0024 --    --   --                         500 16    >0.05 0.00075                                                                             0.02 0.002 0.00009                                                                              --    --   --                         501 20    >0.05 --    >0.1 --    0.00045                                                                              --    --   --                         502 80    --    --    --   --    --     --    --   --                         503 21    0.006 --    0.08 --    0.001  --    >0.01                                                                              --                         504 <100  0.0003                                                                              --    0.05 --    0.00025                                                                              --    0.01 --                         505 14    0.002 --    0.09 --    0.0024 --    >0.01                                                                              --                         506 40    0.03  --    >0.1 --    0.005  --    >0.01                                                                              --                         507 93    0.05  --    >0.1 --    0.002  --    >0.01                                                                              --                         508 >100  --    --    >0.1 --    0.013  --    >0.01                                                                              --                         509 79    >0.05 --    >0.1 --    0.0075 --    >0.01                                                                              --                         510 54    0.05  --    >0.1 --    0.017  --    >0.01                                                                              --                         511 89    0.05  --    >0.1 --    0.0012 --    >0.01                                                                              --                         512 35    >0.05 --    >0.1 --    0.003  >0.05 >0.01                                                                              --                         513 81    >0.05 --    >0.1 --    0.007  >0.05 >0.01                                                                              --                         514 >100  0.003 --    >0.1 --    0.008  >0.05 >0.01                                                                              --                         515 28    >0.05 --    >0.1 --    0.0015 >0.05 >0.01                                                                              --                         516 >100  >0.05 --    >0.1 --    0.008  >0.05 >0.01                                                                              --                         517 80    >0.05 --    0.04 --    0.0008 >0.05 >0.01                                                                              --                         518 >100  >0.05 --    >0.1 --    0.00075                                                                              >0.05 >0.01                                                                              --                         519 60    >0.05 --    >0.1 --    0.0037 >0.05 >0.01                                                                              --                         520 5.5   0.0002                                                                              0.00075                                                                             >0.1 --    >0.1   0.0003                                                                              0.0042                                                                             --                         521 7.5   0.0008                                                                              0.0005                                                                              >0.1 --    0.00005                                                                              0.05  0.01 --                         522 17.5  0.002 --    >0.1 --    >0.1   0.05  >0.01                                                                              --                         523 22    0.001 0.0002                                                                              >0.1 --    0.00015                                                                              >0.05 >0.01                                                                              --                         524 5.2   >0.05 --    >0.1 --    >0.1   >0.05 >0.01                                                                              --                         525 >100  >0.05 --    >0.1 --    <0.1   >0.05 >0.01                                                                              --                         526 8.3   >0.05 --    >0.1 --    >0.1   >0.05 >0.01                                                                              --                         527 47    0.03  --    0.035                                                                              --    0.00065                                                                              >0.05 >0.01                                                                              --                         528 59.1  >0.05 --    >0.1 --    0.0075 >0.05 >0.01                                                                              --                         529 27.7  >0.05 --    >0.1 --    >0.0025                                                                              >0.05 >0.01                                                                              --                         530 9.8   0.0003                                                                              0.00005                                                                             0.005                                                                              --    0.00027                                                                              0.05  >0.01                                                                              --                         531 5     >0.05 0.00037                                                                             >0.1 --    >0.1   >0.05 >0.01                                                                              --                         532 >100  >0.05 --    >0.1 --    <0.1   >0.05 >0.01                                                                              --                         533 60    >0.05 --    >0.1 --    >0.1   >0.05 >0.01                                                                              --                         534 >100  >0.05 --    >0.1 --    <0.1   >0.05 >0.01                                                                              --                         535 41    >0.05 --    >0.1 --    >0.1   >0.05 >0.01                                                                              --                         536 >100  <0.05 --    >0.1 --    <0.1   >0.05 >0.01                                                                              --                         537 20    >0.05 --    >0.1 --    >0.1   >0.05 >0.01                                                                              --                         538 75    >0.05 --    >0.1 --    >0.1   >0.05 >0.01                                                                              --                         539 22    >0.05 --    >0.1 --    >0.1   >0.05 >0.01                                                                              --                         540 >100  >0.05 --    >0.1 --    <0.1   >0.05 >0.01                                                                              --                         541 <100  0.004 --    >0.1 --    0.001  >0.05 >0.01                                                                              --                         542 >100  >0.05 --    >0.1 --    >0.01  >0.05 >0.01                                                                              --                         543 <100  0.003 --    >0.1 --    0.0008 <0.05 >0.01                                                                              --                         544 >100  0.005 --    >0.1 --    >0.1   >0.05 >0.01                                                                              --                         545 <100  0.005 --    >0.1 --    >0.1   >0.05 >0.01                                                                              --                         546 <100  0.001 --    >0.1 --    0.0001 <0.05 0.0032                                                                             --                         547 <100  0.0006                                                                              --    0.05 --    0.0005 <0.05 >0.01                                                                              --                         548 >100  >0.05 --    >0.1 --    <0.1   >0.05 >0.01                                                                              --                         549 <100  >0.05 --    >0.1 --    >0.1   >0.05 >0.01                                                                              --                         550 <100  0.002 --    >0.1 --    0.00034                                                                              --    >0.01                                                                              --                         551 <100  0.0006                                                                              --    0.035                                                                              --    0.00075                                                                              --    >0.01                                                                              --                         552 >100  0.002 --    >0.1 --    0.0016 --    >0.01                                                                              --                         553 <100  0.05  --    0.1  --    <0.1   --    >0.01                                                                              --                         554 >100  0.003 --    0.04 --    0.00075                                                                              --    >0.01                                                                              --                         555 <100  0.0035                                                                              --    >0.1 --    0.002  --    >0.01                                                                              --                         556 <100  0.0035                                                                              --    0.04 --    0.0007 --    >0.01                                                                              --                         557 <100  0.0015                                                                              --    >0.1 --    0.0004 --    >0.01                                                                              --                         558 <100  0.0012                                                                              --    >0.1 --    0.00045                                                                              --    >0.01                                                                              --                         559 <100  0.0035                                                                              --    0.017                                                                              --    0.00027                                                                              --    >0.01                                                                              --                         560 <100  0.0025                                                                              --    <0.1 --    0.0015 --    >0.01                                                                              --                         __________________________________________________________________________     *Compound demonstrated activity in tests against twospotted mite.              (see below)                                                             

The compounds in Tables 1 and 2 were also tested for activity againstthe two-spotted mite [Tetranychus urticae (Koch)] and Western spottedcucumber beetle larvae [Diabrotica undecimpunctata undecimpunctata(Mannerheim)]. Initial testing levels were 0.05% (in solution) againstthe mite, and 25 ppm (in soil) against the beetle. Some compoundsdemonstrated 50% or more mortality against one or the other insect atthe initial testing level, but most did not.

Other compounds within the scope of this invention which have beenprepared and have shown 50% or greater mortality against at least oneinsect in tests as described above are listed below. Most of thesecompounds are analogous to a compound in Table 1 or 2, that is, theyhave the same groups indicated for R₂ and R₃ (or R₄ and R₅ of Table 1),differing only in having different substituents on the phenyl ring fromthe indicated compound. These were:

Analogous to compound 81 in which the substituents on the phenyl ringare: 3-Cl,4-Br; 3-CF₃,4-Br; 4-SO₂ CH₃ ; 2-Cl,4-CF₃ ; 3-F,4-OCH₂ CF₃ ;3-OCH₃,4-Br; 3-Br,4-OCH₃ ; 3-F,4-OCH₃ ; 3-Cl,4-C₂ H₅ ; 2-Cl,5-C₂ H₅ ;3-F,4-OC₂ H₅ ; 4-n-C₃ H₇ ; 2,3,4-F; 3-Cl,4-OC₂ H₅ ; 3-OC₂ H₅,4-Br;3-Br,4-OC₂ H₅ ; 3-OCH₃,4-Cl; 3-OCH₃,4-CF₃ ; 3-OC₂ H₅,4-Cl; 2-NO₂,4-CF₃ ;3-F,4-I; 3-Cl,4-OCHF₂ ; 3-Br,4-C₂ H₅ ; 2,3-F; 3-Br,4-CH₃ ; 3-I,4-CH₃ ;and 4-n-C₃ F₇ ;

Analogous to compound 82 in which the substituents on the phenyl ringare: 4-CH₃ ; 4-OCH₃ ; 2,3-CH₃ ; 2,4-CH₃ ; 3,4-CH₃ ; 3,4-OCH₃ ; 3-C₂ H₅ ;3-CH₃ ; 3-Cl; 4-Br; 3-CF₃,4-Br; 4-I; 3-F; 3-Cl,4-Br; 3-Cl,4-I; 3-I;4-CN; 3-OCH₃ ; 4-SO₂ CH₃ ; 3-OC₂ H₅ ; 3-OCH₃,4-Br; 3-Br,4-OCH₃ ;3-Cl,4-C₂ H₅ ; 3-OCH₃,4-Cl; 3-OCH₃,4-CF₃ ; 3-OCH₃,4-Br; 3-F,4-Cl;3-Br,4-OC₂ H₅ ; 3-Cl,4-OCHF₂ ; 3-F,4-I; 2,3-F; 4-n-C₃ H₇ ; 3-Br,4-C₂ H₅; 3-Br,4-CH₃ ; 4-n-C₄ H₉ ; 3-I,4-CH₃ ; 4 -n-C₃ F₇ ; and 4-OCF₂ CHF₂ ;

Analogous to compound 89 in which the substituents on the phenyl ringare: 4-OCF₃ ; 3-Cl,4-Br; 3-F,4-Br; 3-NO₂,4-F; 3-CF₃ ; 3-F,4-CH₃ ;2-Cl,5-F; 2,5-F; 3-CF₃,4-NO₂ ; 4-t-C₄ H₉ ; 3-CF₃,4-Br; 2-Br,4-t-C₄ H₉ ;2-Br,4-i-C₃ H₇ ; 3,5-CH₃ ; 3-CH₃ ; 2,4-CH₃ ; 3,4-CH₃ ; 3-CH₃,4-Br;2,3-CH₃ ; 4-OCH₃ ; 4-SCH₃ ; 3,4-OCH₃ ; 3-OC₂ H₅ ; 3-OCH₃,4-Br; 4-OC₂ H₅; 4-Cl,4-OC₂ H₅ ; 3-Br,4-OCH₃ ; 3-F,4-OCH₃ ; 3-OCF₃ ; 2-Cl,5-OC₂ H₅ ;3-F,4-OC₂ H₅ ; 4-n-C₃ H₇ ; 3-OCH₃,4-Cl; 3-OCH₃,4-CF₃ ; 3-OC₂ H₅,4-Cl;3-OCH₃,4-Br; 3-Br,4-OC₂ H₅ ; 3-Cl,4-OCHF₂ ; 3-F,4-I; 3-Br,4-C₂ H₅ ;3-Br,4-CH₃ ; 4-n-C₄ H₉ ; and 4-n-C₃ F₇ ;

Analogous to compound 191 in which the substituents on the phenyl ringare: 4-F; 2,3,4-F and 2,4-F,3-Cl;

Analogous to compound 216 in which the substituents on the phenyl ringare: 3,4-(-OCH₂ O-); 3-Br; 4-Cl; 4-F; 4-CH₃ ; 2,4-CH₃ ; 4-OCH₃ ; 2,3-CH₃; 3,4-CH₃ ; 3-C₂ H₅ ; 3-SCH₃ ; 3-CH₃ ; 3-Cl,4-I; 3-OCH₃ ; 4-SCH₃ ;2-Cl,4-CF₃ ; 3-OCH₃,4-Br; 3-F,4-OCH₃ ; 3-Br,4-OCH₃ ; 3-OCF₃ ; 3-Cl,4-C₂H₅ ; 3-F,4-OC₂ H₅ ; 3-OCH₃,4-Cl; 3-CF₃,4-OCH₃ ; 3-OC₂ H₅,4-Cl; 3-OC₂H₅,4-Br; 3-Br,4-OC₂ H₅ ; 3-F,4-I; 3-Br,4-C₂ H₅ ; 4-n-C₄ H₉ ; 2-F,4-CH₃ ;2-F,4-Cl; 2,4-F; 3-I,4-CH₃ ; and 4-O-n-C₃ H₇ ;

Analogous to compound 217 in which the substituents on the phenyl ringare 3-Cl,4-C₂ H₅ ; 4-CF₃ ; 3-Cl,4-CH₃ and 4-OCF₃ ;

Analogous to compound 238 in which the substituents on the phenyl ringare: 3-CF₃ ; 3-F; 3-I; 3-F,4-CF₃ ; and 4-Br;

Analogous to compound 239 in which the substituents on the phenyl ringare: 3-CF₃ ; 3,4-F; 3-OCH₃ ; 3-CH₃ ; 4-OC₂ H₅ ; 2-Cl; 2-CH₃ ; 3-NO₂,4-F;3-4-Cl; 3-F,4-CF₃ ; 4-t-C₄ H₉ ; 3-Cl; 3-F; 3-CF₃,4-Br; 4-Br; 4-I; 4-C₂H₅ ; 3-F,4-Br; 3,4-Br; 3-CF₃,4-Cl; 4-OCF₃ ; 3-SCH₃ ; 4-F; 2,4-CH₃ ;4-CH₃ ; 3,4-CH₃ ; 3-CH₃,4-Br; 3-Cl,4-OCH₃ ; 2,3-CH₃ ; 4-OCH₃ ; 4-SCH₃ ;3-Cl,4-OCH₂ CF₃ ; 2-Cl,4-CF₃ ; 3-OCH₃,4-Br; 3-Br,4-OCH₃ ; 3-OCF₃ ;3-Cl,4-C₂ H₅ ; 3-F,4-OC₂ H₅ ; 2,3,4-F; 3-F,4-CH₃ ; 3-CF₃,4-OCH₃ ; 3-OC₂H₅,4-Cl; 3-OC₂ H₅,4-Br; 3-Br,4-OC₂ H₅ ; 3-Cl,4-OCHF₂ ; 3-F,4-I;3-Br,4-C₂ H₅ ; 4-n-C₃ H₇ ; 3-Br,4-CH₃ ; 4-n-C₄ H₉ ; 2-F,4-CH₃ ;2-F,4-Cl; 3-I,4-CH₃ ; 4-n-C₃ H₇ ; and 4-OCF₂ CHF₂ ;

Analogous to compound 267 in which the substituents on the phenyl ringare: 4-I; 4-C₂ H₅ ; 3,4-Br, 3-Cl,4-I; 3-I; 3-SCH₃ ; 2,4-CH₃ ; 2-C₂ H₅ ;3-OCH₃ ; 4-SO2CH₃ ; 2-Cl,4-CF₃ ; 3,4-OCH₃ ; 3-OC₂ H₅ ; 3-OCH₃,4-Br;3-Br,4-OCH₃ ; 3-F,4-OCH₃ ; 4-OCH₂ CF₃ ; 3-Cl,4-OCH₃ ; 3-F,4-CH₃ ;3-OCH₃,4-Cl; 3-CF₃,4-OCH₃ ; 3-OC₂ H₅,4-Cl; 3-OC₂ H₅,4-Br; 3-F,4-Cl;2-NO2,4-CF₃ ; 3-Br,4-OC₂ H₅ ; 3-F,4-I; 3-Br,4-C₂ H₅ ; 2,3-F; 4-n-C₃ H₇ ;3-Br,4-CH₃ ; 4-n-C₄ H₉ ; 2-F,4-Cl; 3,5-F; 3-I,4-CH₃ ; 4-n-C₃ F₇ ; and4-OCF₂ CHF₂ ;

Analogous to compound 274 in which the substituents on the phenyl ringare 3-Cl,4-F;

Analogous to compound 447 in which the substituent on the phenyl ring is4-I;

Analogous to compound 461, in which the substituent on the phenyl ringis 4-CF₃ ;

Analogous to compound 462 in which the substituents on the phenyl ringare: 3-Cl,4-OCHF₂ ; 3-Cl,4-CH₃ ; 2,3-CH₃ ; 3-CF₃,4-Br; 3,4-(-OCH₂ O-);3-NO₂ ; 2-Cl; 2-CH₃ ; 3-CF₃,4-F; 3-F,4-CH₃ ; 3-Cl,4-OCH₃ ; 3,4-OCH₃ ;4-Br; 4-CF₃ ; 2,4-F,3-Cl; 4-CN; 3-F,4-Br; 4-C₂ H₅ ; 3-CH₃,4-F; 3-Br;4-I; 2-Cl,4-CF₃ ; 3,4-F; 3-Cl; 3-C₂ H₅ ; 4-F; 4-CH₃ ; 3-CH₃ ; 3-OCH₃ ;3-Cl,4-OCH; 3-F; 4-OCH₂ CF3; 4-OC₂ H₅ ; 3,4-OC₂ H₅ ; 3,4-CH₃ ; 3-Cl,4-I;2,4-Cl and 3,4-Cl;

Analogous to compound 510 in which the substituent on the phenyl ring is3-Cl,4-F;

Analogous to compound 516 in which the substituents on the phenyl ringare 3,4-(-OCH₂ O-) and 2,4-F,3-Cl;

Analogous to compound 517 in which the substituents on the phenyl ringare 3,4-(-OCH₂ O-) and 4-CF₃ ;

Analogous to compound 518 in which the substituents on the phenyl ringare 2,4-F,3-Cl;

Analogous to compound 520 in which the substituent on the phenyl ring is3-CF₃ ;

And the compounds shown below in Table 4.

                  TABLE 4                                                         ______________________________________                                         ##STR156##                                                                   Phenyl Subst.  R.sub.2       R.sub.4 R.sub.5                                  ______________________________________                                        3-Cl,4-F       CHCl.sub.2    H       4-F                                      4-i-C.sub.3 H.sub.7                                                                          sec.-C.sub.4 H.sub.9                                                                        H       4-F                                      4-i-C.sub.3 H.sub.7                                                                          C.sub.2 H.sub.5                                                                             H       H                                        4-i-C.sub.3 H.sub.7                                                                          CHBrCH.sub.3  H       4-F                                      4-i-C.sub.3 H.sub.7                                                                          CHBrCH.sub.3  H       H                                        4-CF.sub.3     C(CH.sub.3)CH.sub.2                                                                         4-F     4-F                                      4-F            C(CH.sub.3)CH.sub.2                                                                         H       H                                        4-F            C(CH.sub.3)CH.sub.2                                                                         4-F     4-Cl                                     4-F            C(CH.sub.3)CH.sub.2                                                                         4-F     H                                        3,4-F          C(CH.sub.3)CH.sub.2                                                                         H       H                                        3,4-F          C(CH.sub.3)CH.sub.2                                                                         4-F     4-Cl                                     3,4-F          C(CH.sub.3)CH.sub.2                                                                         4-F     H                                        3,4-(OCH.sub.2 O)                                                                            C(CH.sub.3)CH.sub.2                                                                         H       H                                        3,4-(OCH.sub.2 O)                                                                            C(CH.sub.3)CH.sub.2                                                                         4-F     4-Cl                                     3,4-(OCH.sub.2 O)                                                                            (CCH.sub. 3)CH.sub.2                                                                        4-F     H                                        4-OCF.sub.3    C(CH.sub.3)CH.sub.2                                                                         H       H                                        4-OCF.sub.3    C(CH.sub.3)CH.sub.2                                                                         4-F     4-Cl                                     4-OCF.sub.3    C(CH.sub.3)CH.sub.2                                                                         4-F     H                                        3-Cl,4-F       CHC(CH.sub.3).sub.2                                                                         H       H                                        3-Br,4-F       C(CH.sub.3)CH.sub.2                                                                         H       H                                        3-Br,4-F       C(CH.sub.3)CH.sub.2                                                                         4-F     4-Cl                                     3-Br,4-F       C(CH.sub.3)CH.sub.2                                                                         4-F     H                                        3-Br,4-F       C(CH.sub.3)CH.sub.2                                                                         H       4-Cl                                     3-F,4-OCHF.sub.2                                                                             i-C.sub.3 H.sub.7                                                                           H       H                                        3-F,4-OCHF.sub.2                                                                             i-C.sub.3 H.sub.7                                                                           4-F     4-F                                      3-F,4-OCHF.sub.2                                                                             i-C.sub.3 H.sub.7                                                                           4-F     4-Cl                                     3-F,4-OCHF.sub.2                                                                             i-C.sub.3 H.sub.7                                                                           H       4-F                                      3-F,4-OCHF.sub.2                                                                             i-C.sub.3 H.sub.7                                                                           4-F     H                                        3-F,4-OCHF.sub.2                                                                             i-C.sub.3 H.sub.7                                                                           H       4-Cl                                     3-CF.sub.3     C(CH.sub.3)CH.sub.2                                                                         H       4-Cl                                     4-OCHF.sub.2   i-C.sub.3 H.sub.7                                                                           H       H                                        4-OCHF.sub.2   i-C.sub.3 H.sub.7                                                                           H       4-F                                      4-OCHF.sub.2   i-C.sub.3 H.sub.7                                                                           4-F     H                                        4-OCHF.sub.2   i-C.sub.3 H.sub.7                                                                           H       4-Cl                                     3-Cl,4-OCF.sub.3                                                                             i-C.sub.3 H.sub.7                                                                           4-F     4-F                                      3-Cl,4-OCF.sub.3                                                                             i-C.sub.3 H.sub.7                                                                           4-F     4-Cl                                     3-Cl,4-OCH.sub.2 CClCH.sub.2                                                                 i-C.sub.3 H.sub.7                                                                           4-F     4-F                                      3-Cl,4-OCH.sub.2 CCl CH.sub.2                                                                i-C.sub.3 H.sub.7                                                                           4-F     4-Cl                                     4-OCH.sub.2 CClCH.sub.2                                                                      i-C.sub.3 H.sub.7                                                                           4-F     4-F                                      4-OCH.sub.2 CClCH.sub.2                                                                      i-C.sub.3 H.sub.7                                                                           4-F     4-Cl                                     4-C.sub.2 F.sub.5                                                                            i-C.sub.3 H.sub.7                                                                           4-F     4-Cl                                     4-C.sub.2 F.sub.5                                                                            i-C.sub.3 H.sub.7                                                                           4-F     4-F                                      3,4-Cl         CH(CH.sub.3)CF.sub.3                                                                        4-F     4-F                                      3-Cl,4-F       CH(CH.sub.3)CF.sub.3                                                                        4-F     4-F                                      2-F,4-CH.sub.3 i-C.sub.3 H.sub.7                                                                           H       H                                        2-F,4-Cl       i-C.sub.3 H.sub.7                                                                           H       H                                        3-Cl,4-F       C(CH.sub.3)CH.sub.2                                                                         F       F                                        2,4-F          i-C.sub.3 H.sub.7                                                                           H       4-Cl                                     3,5-F          i-C.sub.3 H.sub.7                                                                           4-F     H                                        3-I,4-CH.sub.3 i-C.sub.3 H.sub.7                                                                           H       4-F                                      4-n-C.sub.3 F.sub.7                                                                          i-C.sub.3 H.sub.7                                                                           4-F     4-F                                      4-OCF.sub.3    C(CH.sub.3)CH.sub.2                                                                         H       4-Cl                                     4-OCF.sub.3    C(CH.sub.3)CH.sub.2                                                                         H       4-F                                      4-OCF.sub.3    C(CH.sub.3)CH.sub.2                                                                         4-F     4-F                                      3,4-F          C(CH.sub.3)CH.sub.2                                                                         H       4-Cl                                     3,4-F          C(CH.sub.3)CH.sub.2                                                                         H       4-F                                      3,4-F          C(CH.sub.3)CH.sub.2                                                                         4-F     4-F                                      2,4-F,3-Cl     C(CH.sub.3)CH.sub.2                                                                         H       H                                        2,4-F,3-Cl     C(CH.sub.3)CH.sub.2                                                                         4-F     H                                        2,4-F,3-Cl     C(CH.sub.3) CH.sub.2                                                                        4-F     4-Cl                                     3-CF.sub.3     C(CH.sub.3)CH.sub.2                                                                         H       H                                        3-CF.sub.3     C(CH.sub.3)CH.sub.2                                                                         4-F     H                                        3-CF.sub.3     C(CH.sub.3)CH.sub.2                                                                         4-F     4-Cl                                     3-Br           C(CH.sub.3)CH.sub.2                                                                         H       H                                        3-Br           C(CH.sub.3)CH.sub.2                                                                         4-F     H                                        3-Br           C(CH.sub.3)CH.sub.2                                                                         4-F     4-Cl                                     2,3-F          C(CH.sub.3)CH.sub.2                                                                         H       H                                        2,3-F          C(CH.sub.3)CH.sub.2                                                                         4-F     H                                        2,3-F          C(CH.sub.3)CH.sub.2                                                                         4-F     4-Cl                                     4-SCHF.sub.2   i-C.sub.3 H.sub.7                                                                           4-F     4-Cl                                     4-SCHF.sub.2   i-C.sub.3 H.sub.7                                                                           4-F     4-F                                      3-Cl,4-OCF.sub.3                                                                             i-C.sub.3 H.sub.7                                                                           4-F     H                                        3-Cl,4-OCF.sub.3                                                                             i-C.sub.3 H.sub.7                                                                           H       Cl                                       4-OCF.sub.2 CHF.sub.2                                                                        i-C.sub.3 H.sub.7                                                                           H       H                                        4-OCF.sub.3    C.sub.2 H.sub.5                                                                             H       H                                        3-CF.sub.3, 4-OCF.sub.2 Br                                                                   i-C.sub.3 H.sub.7                                                                           4-F     4-F                                      3-CF.sub.3,4-OCF.sub.2 Br                                                                    i-C.sub.3 H.sub.7                                                                           H       H                                        3-F,4-OCF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                           4-F     4-F                                      3-F,4-OCF.sub.3                                                                              i-C.sub.3 H.sub.7                                                                           H       H                                        3-Br,4-OCF.sub.3                                                                             i-C.sub.3 H.sub.7                                                                           4-F     4-F                                      3-Br,4-OCF.sub.3                                                                             i-C.sub.3 H.sub.7                                                                           H       H                                        3-Br,4-OCF.sub.2 Br                                                                          i-C.sub.3 H.sub.7                                                                           4-F     4-F                                      3-Br,4-OCF.sub.2 Br                                                                          i-C.sub.3 H.sub.7                                                                           H       H                                        ______________________________________                                    

For information, the following Table 5 lists a very small number ofcompounds within the definition of the class of this invention which didnot produce 50% or greater mortality in an insecticidal evaluation testto date.

                                      TABLE 5                                     __________________________________________________________________________     ##STR157##                                                                   Phenyl Subst.                                                                        R.sub.2  R.sub.3                                                       __________________________________________________________________________    4-Cl   CHCl.sub.2                                                                              ##STR158##                                                   4-OCF.sub.3                                                                          CHClCH.sub.2 CH.sub.2 Cl                                                                ##STR159##                                                   2,3-Cl i-C.sub.3 H.sub.7                                                                       ##STR160##                                                   H      C(CH.sub.3)2CH.sub.2 Cl                                                                 ##STR161##                                                   3,5-CF.sub.3                                                                         i-C.sub.3 H.sub.7                                                                       ##STR162##                                                   3-Cl   i-C.sub.3 H.sub.7                                                                       ##STR163##                                                   3,5-Cl i-C.sub.3 H.sub.7                                                                       ##STR164##                                                   2,4-Cl i-C.sub.3 H.sub.7                                                                       ##STR165##                                                   3,4-Cl i-C.sub.3 H.sub.7                                                                       ##STR166##                                                   3-Cl   t-C.sub.4 H.sub.9                                                                       ##STR167##                                                   3,4-OCH.sub.3                                                                        i-C.sub.3 H.sub.7                                                                       ##STR168##                                                   4-Cl   C(CH.sub.3)CH.sub.2                                                                     ##STR169##                                                   3-Cl,4-F                                                                             i-C.sub.3 H.sub.7                                                                       ##STR170##                                                   3-CF.sub.3                                                                           i-C.sub.3 H.sub.7                                                                       ##STR171##                                                   __________________________________________________________________________

The insecticidal activity, and therefore the inclusion of a compound notmentioned specifically herein within the class of compounds of thisinvention, as determined by the general formula (I), may be determinedby evaluating such a compound using one or more of the above-describedprocedures. If a test compound demonstrates activity against one or moreof the insects mentioned, by virtue of causing 50 percent or greatermortality at the initial evaluation level, it is considered"insecticidal" for the purposes of this invention.

In practice, a pure compound (active compound) can be used as aninsecticide. However, in general, the compounds are first formulatedwith one or more inert (i.e. non-chemically reactive, plant compatibleor herbicidally inert) carriers or diluents suitable for insecticidaluse, before being applied.

The compositions or formulations, including a compound as describedherein, may take any one of a number of solid or liquid forms. Examplesof solid forms are dusts, granules, tablets, powders and the like.Examples of liquid forms are emulsions, solutions, suspensions,flowables, emulsifiable concentrates and pastes. Such compositions maycontain, in addition to the active compound or compounds, variouscarriers or diluents; surface-active agents (wetting agents, dispersingagents and/or emulsifying agents); solvents (water, or organic solventssuch as aromatic solvents or chlorinated aliphatic solvents); adhesives;thickeners; binders; anti-foaming agents; and other substances asmentioned herein. Solid carriers or diluents included in suchcompositions or formulations may include, for example, ground naturalminerals such as kaolins, alumina, calcined diatomaceous earth, calciumcarbonate, silica, kieselguhr, clays, etc.; ground synthetic mineralssuch as various silicates and alumino-silicates and ground vegetableproducts such as bark, cornmeal, sawdust, cellulose powder and the like.Compositions containing sorptive clays will usually also contain astabilizer, such as a glycol, to prevent or minimize degradation of theactive ingredient.

To manufacture solid compositions, the active compounds are mixed withsolid carriers or diluents such as those mentioned above and the mixtureis ground to the appropriate size. Granules can be manufactured bydissolving an active compound in an organic solvent and applying themixture, for example, by atomization, onto an absorptive granulatedinert material, such as silica. Adhesives may be utilized to assist inthe incorporation of the compound onto the solid particles.

Wettable powders and pastes are obtained by mixing and grinding anactive compound with one or more dispersing agents and/or solid carriersor diluents. Also included may be wetting agents and/or dispersingagents, for example, lignins, methyl cellulose, naphthalenesulfonic acidderivatives, fatty alcohol sulfates and various types of alkali andalkaline earth metal salts of fatty acids.

Emulsifiable concentrates are generally obtained by dissolving theactive compound in an organic solvent, for example, butanol,cyclohexanone, xylenes, or higher boiling aromatic hydrocarbons. Toobtain suspensions or emulsions in water, wetting agents may also beadded.

Flowables are prepared by mixing an active compound with one or moredispersing agents and/or solid additives, and a liquid (which may bewater or an organic solvent) in which the active compound is relativelyinsoluble, and grinding the mixture.

Both liquid and solid compositions may be in microcapsule orencapsulated form, to permit release of the enclosed active compound ata controlled rate over a period of time. Liquid compositions of thistype contain encapsulated droplets of approximately 1-50 microns indiameter, including the active compound and optionally a solvent. Theencapsulating material is an inert porous membrane of a polymericmaterial.

Solid encapsulated compositions generally take the form of granules, inwhich the liquid containing the active component is trapped in the poresof the granular support by a porous polymeric membrane through which theactive ingredient may migrate at a controlled rate, or which membranebreaks down at a controlled rate to permit escape of the activeingredient.

Typical encapsulating materials include natural and synthetic rubbers,cellulosic materials, styrene-butadiene copolymers, polyacrylonitriles,polyacrylates, polyamides, polyisocyanates, polyurethanes, mixedcopolymers of the foregoing and starch xanthates.

It is possible to use highly concentrated liquid compositions containingup to about 95% by weight of the active compound, or even the 100%active compound alone, when applying the compound in the form of afinely divided liquid by use of various atomizing equipment, for exampleby airplane spraying techniques. For other purposes, however, thevarious types of compositions which can be utilized for these compoundswill contain varying amounts of the compound according to the type ofcomposition and the intended use.

In general, insecticidal compositions may contain from 5 to 95% of theactive compound, more preferably from 10 to 85%. Some typicalcompositions will contain an active compound as follows: wettablepowders: 25 to 80% active compound; oil suspensions, emulsions,solutions, flowables, and emulsifiable concentrates: 5 to 85% activecompound; aqueous suspensions: 20 to 50% active compound; dusts andpowders: 5 to 20% active compound; granules and pellets: 5 to 20% activecompound.

In addition to the active compound and the various agents utilized inpreparing compositions and formulations mentioned, such compositions mayalso contain one or more other active compounds of the type mentionedherein as well as other active pesticidal agents, such as herbicides,fungicides, insecticides, acaricides, nematocides, bactericides, andplant growth regulators. The particular pesticide included in themixture will depend upon its intended utility and the type ofcomplementary action required. Examples of suitable insecticides includethe following:

(a) natural pyrethrins or pyrethroids such as permethrin, fenvalerate,deltamethrin, cyhalothrin, biphenthrin, fenpropathrin, cyfluthrin,tefluthrin, empenthrin, ethofenprox, tetramethrin, bioallethrin,fenfluthrin, prallethrin,5-benzyl-3-furylmethyl-(E)-(1R,3S)-2,2-dimethyl-3-(2-oxothiolan-3-ylidene- methyl)cyclopropane carboxylate and pentafluorobenzyl(cis)-3-[-2-fluoro-2-(methoxycarbonyl)ethenyl]-2,2-dimethylcyclopropanecarboxylate;

(b) organophosphates such as profenofos, sulprofos, phosmet, dichlorvos,methyl parathion, azinphos-methyl, dimeton-s-methyl, heptenophos,thiometon, fenamiphos, monocrotophos, triazophos, methamidophos,dimethoate, phosphamidon, malathion, chlorpyrifos, phosalone,fensulfothion, fonofos, phorate, phoxim, pyrimiphosmethyl, fenitrothionand diazinon;

(c) carbamates (including aryl carbamates) such as pirimicarb,cloethocarb, carbofuran, ethiofencarb, aldicarb, thiofurox, carbosulfan,bendiocarb, fenobucarb, propoxur and oxamyl;

(d) benzoyl ureas such as triflumuron, chlorofluazuron;

(e) organic tin compounds such as cyhexatin, fenbutatin oxide andazocyclotin;

(f) macrolides such as avermectins or milbemycins, for example such asabamectin, avermectin, and milbemycin;

(g) hormones and synthetic mimics thereof such as juvenile hormone,juvabione, ecdysones, methoprene and hydroprene;

(h) pheromones; and

(i) organochlorine compounds such as benzene hexachloride, DDT,chlordane or dieldrin.

In addition to the major chemical classes of insecticide listed above,other insecticides having particular targets may be employed in themixture if appropriate for the intended utility of the mixture. Forinstance selective insecticides for particular crops, for examplestemborer specific insecticides for use in rice such as cartap orbuprofesin, can be employed. Alternatively, insecticides specific forparticular insect species/stages, for example ovolarvicides such asclofentezine, amitraz, chlordimeform flubenzimine, hexythiazox andtetradifon, motilicides such as dicofol or propargite, adulticides suchas bromopropylate, chlorobenzilate, or insect growth regulators such ashydramethylon, cyromazine, methoprene, chlorofluazuron and diflubenzuronmay also be included in the compositions. Such compounds may alsocontain soil disinfectants or fumigants and may further containfertilizers, thus making it possible to provide multi-purposecompositions containing one or more of the active compounds describedherein as well as, optionally, other pesticides and also fertilizers,all intended and formulated for use at the same locus.

Control of insect pests is accomplished by applying a compositioncontaining an insecticidally effective amount of an active compound asdescribed herein to the insect, to a locus at which insecticidal controlis desired, or to food sources (including seeds) on which the insectsfeed. For use in the last mentioned manner it is preferable to utilize acompound which is not volatile. Thus, control may be achieved by directapplication of the active compounds to the insects and indirectly byapplication of the compounds to a locus to be protected (such as croplands, grass ranges and forests), to a source of food for insects or toother insect habitats (for example, breeding or swarming areas). Therates of application of the active compound, and the concentrationapplied, will vary according to whether the compound or composition isbeing directly applied to the insect or indirectly, to a locus, food orhabitat. In the latter case the rate of the application, depending onthe nature of the insect or insects to be controlled, and the plantenvironment, will generally vary from about 0.01 to about 100 pounds peracre (about 0.011 to about 111 kg/ha).

It should be noted that the active compound need not be insecticidallyactive per se to effect insect control. The purposes of this inventionare fully served if such compounds are rendered active by externalinfluences, such as light or heat, or by some physiological action whichoccurs when the compound is ingested into the body of the insect.

Compounds of this invention could be used to control a variety ofinsects such as:

Myzus persicae (aphid)

Aphis gossypii (aphid)

Aphis fabae (aphid)

Megoura viceae (aphid)

Aedes aegypti (mosquito)

Anopheles spp. (mosquitos)

Culex spp. (mosquitos)

Dysdercus fasciatus (capsid)

Musca domestica (housefly)

Pieris brassicae (white butterfly)

Plutella maculipennis (diamond back moth)

Phaedon cochlaeriae (mustard beetle)

Aonidiella spp. (scale insects)

Trialeuroides spp. (white flies)

Bemisia tabaci (white fly)

Blattella germanica (cockroach)

Periplaneta americana (cockroach)

Blatta orientalis (cockroach)

Spodoptera littoralis (cotton leafworm)

Heliothis virescens (tobacco budworm)

Chortiocetes terminifera (locust)

Diabrotica spp. (rootworms)

Agrotis spp. (cutworms)

Chilo supressalis (stem borer

Chilo partellus (maize stem borer)

Nilaparvata lugens (planthopper)

Nephottex virescens (leafhopper

Nephotettix cincticeps (leafhopper)

Panonychus ulmi (European red mite)

Panonychus citri (citrus red mite)

Tetranychus urticae (two-spotted spider mite)

Tetranychus cinnabarinus (carmine spider mite)

Phyllcoptruta oleivora (citrus rust mite)

Polyphagotarsonemus latus (broad mite)

Brevipalpus spp. (mites).

Compositions containing one or more of the active compounds described,in an insecticidally effective amount, may be applied to the plant,locus or insect habitat in any conventional manner.

When used in connection with crop or other plant protection, applicationmay be made in a preventive (i.e. before infestation) or eradicativemanner (i.e., after infestation). Thus, powders and various liquidcompositions containing the active compound can be applied by the use ofpower dusters, boom and hand sprayers and spray dusters, or applied fromairplanes as dusts or sprays. When applied in the latter method they maybe effective in very low dosages.

Compositions including active compounds may also be applied by additionto irrigation waters supplied to the field to be treated. This method ofapplication permits penetration of the compounds into the soil as thewater is absorbed therein.

Compositions including active compounds may additionally be used toprotect plant seeds from being attacked by soil-borne insect pests afterplanting and during germination, by applying the composition to theseeds as a seed dressing. This is performed generally by mixing theseeds with an active composition in either liquid or solid form(preferably liquid) in a suitable mixing apparatus. Liquid compositionsfor this purpose may contain an adhesive or sticking agent, such asmethyl cellulose, ethyl cellulose, etc., to assist the composition inadhering to the seed. If a solid composition is utilized for thispurpose, an adhesive agent may be sprayed on the seeds during or aftermixing.

For use as a soil insecticide, the active compound, or compositionscontaining it, may be mixed with the soil in any conventional manner,before, during or after planting of the plant seeds. Liquid compositionsmay be applied by spraying onto the surface or by incorporation inirrigation or sprayed water. Solid or liquid compositions containing anactive compound may be incorporated into the soil prior to or duringplanting by discing, plowing or other mixing operations, in order tolocate the active ingredient below the surface of the soil so as to bemost effective in controlling undesirable larvae.

Some examples of compositions containing the active compounds of thisinvention are:

    ______________________________________                                        Component               Weight %                                              ______________________________________                                        Composition A: Granular Solid                                                 Active compound         10                                                    attapulgite clay granules                                                                             85                                                    triethylene glycol       5                                                    Total                    100%                                                 Composition B: Wettable Powder                                                Active compound         80                                                    wetting agent (sodium dialkyl-                                                                         1                                                    naphthalene sulfonate)                                                        dispersing agent (sodium                                                                               4                                                    lignosulfonate)                                                               diluent (aluminum magnesium                                                                           15                                                    silicate)                                                                     Total                    100%                                                 Composition C: Dilute Solution                                                Active compound          5                                                    solvent (xylene)        95                                                    Total                    100%                                                 Composition D: Emulsifiable Concentrate                                       Active compound         50                                                    Emulsifier (blend of metal                                                                            10                                                    sulfonates and polyoxy-                                                       ethylene ethers)                                                              solvent (xylene)        40                                                    Total                    100%                                                 Composition E: Concentrated Solution                                          Active compound         90                                                    solvent (xylene)        10                                                    Total                    100%                                                 ______________________________________                                    

What is claimed is:
 1. A compound having the formula ##STR172## in whichR₁ is naphthyl, optionally substituted by up to 2 halogens; or phenyl,optionally substituted by one or more of: C₂ -C₅ carboalkoxy, C₁ -C₄alkylsulfonyl, C₁ -C₄ haloalkylsulfonyl, C₂ -C₅ alkylcarbonyl, C₂ -C₄alkenyl, C₃ -haloalkenoxy; C₁ -C₄ haloalkylthio, C₃ -C₆ cycloalkyl,phenyl, mono-substituted phenyl, pyridyloxy, C₂ -C₄ alkyleneoxy, C₁ -C₂perhaloalkyleneoxy; C₁ -C₄ alkylenedioxy, C₁ -C₃ haloalkylenedioxy, C₂-C₄ alkylene, amido, nitro, cyano, up to two C₁ -C₄ alkylthio groups, upto three C₁ -C₄ alkoxy groups, up to three C₁ -C₄ haloalkoxy groups, upto three C₁ -C₄ alkyl groups, up to three C₁ -C₄ haloalkyl groups, or upto five halogens;R₂ is methyl; ethyl; n-propyl; C₃ -C₇ branched alkyl;C₁ -C₆ haloalkyl, cyclobutyl substituted by up to 4 methyl groups or upto 2 halogens, cyclobutyl, cyano, C₂ -C₄ alkoxyalkyl, C₂ -C₆ alkenyl orC₂ -C₆ haloalkenyl; and R₃ is(a) ##STR173## in which m is 0 or 1; A, Band C are each carbon or nitrogen, provided that A, B and C are not allnitrogen and if two of A, B and C are nitrogen, then A and C arenitrogen; R₄ is hydrogen, monohalo or dihalo; R₆ is hydrogen, methyl,fluoro or ethynyl; and R₇ is(i) ##STR174## in which D and E are eachcarbon or nitrogen provided that both D and E are not nitrogen, andfurther provided that if any of A, B or C is nitrogen, then D and E areboth carbon; andR₅ is hydrogen, C₁ -C₄ alkyl, C₁ -C₄ alkoxy,trifluoromethyl, cyano, C₁ -C₄ alkylthio, C₁ -C₄ alkylsulfonyl, or mono-or polyhalo; (ii) ##STR175## in which R₈ is hydrogen or halogen; or(iii) --O--CH₂ --CH═CH₂ ; (b) ##STR176## in which (i) R₉ is 4-fluoro,4-methoxymethyl, or 4-propargyl, and R₁₀ is fluoro or(ii) R₉ is 3- or4-allyl, 3- or 4-propargyl, or 3- or 4-(mono- or dihalo)allyl, and R₁₀is hydrogen or fluoro; (c) ##STR177## (d) 4-phenoxy-2-butyn-2-yl; (e)3-bromo-4-fluorobenzyl; (f) 4-(benzyloxy)benzyl; (g)4-(4-fluorobenzyloxy)benzyl; (h)4-(4-trifluoromethyl-2-pyridyloxy)benzyl; or (j) ##STR178## providedthat: (i) R₁ is not 2,3-dichlorophenyl, 2,6-difluorophenyl, 2,6-di(C₁-C₄ alkyl)phenyl, 2,4,6-tribromophenyl or 2,4,6-tri(C₁ -C₄ alkoxy)phenyl;(ii) when R₂ is tertiary butyl, R₁ is not phenyl, 3-methylphenyl,4-(n-butyl)phenyl or 4-(t-butyl)phenyl; and (iii) when R₂ is a C₅ alkylgroup, R₁ is not 4-isopropylphenyl.
 2. A compound according to claim 1further in which R₁ is not 2,6-disubstituted phenyl,2,3,6-trisubstituted phenyl or 2,4,6-trisubstituted phenyl.
 3. Acompound according to claim 1 in which R₁ is ##STR179## wherein R₁₁ ishydrogen, halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄haloalkoxy, C₁ -C₄ alkylthio, C₁ -C₄ haloalkylthio, C₂ -C₅ carboalkoxy,C₂ -C₅ alkylcarbonyl, nitro or cyano; R₁₂ is hydrogen, halogen, C₁ -C₄alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄alkylthio, C₁ -C₄ haloalkylthio, C₃ -haloalkenoxy; nitro, cyano, C₁ -C₄alkylsulfonyl, C₂ -C₅ alkylcarbonyl or C₂ -C₅ carboalkoxy; and R₁₃ ishydrogen, halogen, C₁ -C₄ haloalkyl or C₁ -C₄ alkoxy, or R₁₁ and R₁₂taken together are C₂ -C₄ alkylene, C₂ -C₄ alkyleneoxy, C₁ -C₂perhaloalkyeneoxy; C₁ - C₄ alkylenedioxy or halo-C₁ -C₃ alkylenedioxy;and R₁₄ is hydrogen or fluoro; provided that R₁₁, R₁₂ and R₁₃ are notall hydrogen.
 4. A compound according to claim 3 in which R₁₃ ishydrogen and R₁₁ and R₁₂ are other than hydrogen.
 5. A compoundaccording to claim 3 in which R₁₁ and R₁₃ are hydrogen.
 6. A compoundaccording to claim 3 in which R₁₂ and R₁₃ are hydrogen.
 7. A compoundaccording to claim 3 in which R₁₂ is a C₁ -C₂ polyhaloalkoxy groupcontaining at least one fluorine atom and R₁₃ is hydrogen or halogen. 8.A compound according to claim 7 in which R₁₁ is halogen, C₁ -C₄ alkyl,C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy, R₁₃ is hydrogenand R₁₄ is hydrogen.
 9. A compound according to claim 8 in which R₂ isethyl, isopropyl, isopropenyl, or dichloromethyl.
 10. A compoundaccording to claim 3 in which R₁₁ is chloro, R₁₂ is trifluoromethoxy,R₁₃ is hydrogen and R₁₄ is hydrogen.
 11. A compound according to claim10 in which R₂ is ethyl, isopropyl, isopropenyl, or dichloromethyl. 12.A compound according to claim 3 in which R₁₁ is hydrogen or halogen, R₁₂is hydrogen, halogen, C₁ -C₄ alkyl or C₁ -C₄ haloalkoxy; R₁₃ is hydrogenand R₁₄ is fluoro.
 13. A compound according to claim 12 in which R₁₂ isfluoro.
 14. A compound according to claim 12 in which R₁₁ and R₁₂ arefluoro.
 15. A compound according to claim 12 in which R₁₂ is a C₁ -C₂polyhaloalkoxy group containing at least one fluorine atom and R₁₃ ishydrogen.
 16. A compound according to claim 12 in which R₂ is ethyl,isopropyl, isopropenyl, or dichloromethyl.
 17. A compound according toclaim 1 in which R₂ is ethyl, isopropyl, secondary butyl,dichloromethyl, trifluoromethyl, pentafluoroethyl, 2-fluoro-2-propyl,isopropenyl, cyclopropyl, mono-methyl-substituted cyclopropyl ortetramethyl-substituted cyclopropyl.
 18. A compound according to claim 3in which R₂ is isopropyl, isopropenyl, or dichloromethyl.
 19. A compoundaccording to claim 18 in which R₂ is isopropyl or isopropenyl.
 20. Acompound according to claim 1 in which R₃ is ##STR180##
 21. A compoundaccording to claim 17 in which R₃ is ##STR181##
 22. A compound accordingto claim 21 in which R₃ is ##STR182##
 23. A compound according to claim22 in which R₃ is ##STR183##
 24. A compound according to claim 23 inwhich R₄ is hydrogen.
 25. A compound according to claim 23 in which R₅is hydrogen.
 26. A compound according to claim 23 in which R₄ and R₅ areboth hydrogen.
 27. A compound according to claim 23 in which R₄ and R₅are both monohalo.
 28. A compound according to claim 27 in which R₄ andR₅ are both 4-fluoro.
 29. A compound according to claim 27 in which R₄is 4-fluoro and R₅ is 4-chloro.
 30. A compound according to claim 23 inwhich R₄ is 4-fluoro and R₅ is difluoro.
 31. A compound according toclaim 22 in which R₃ is ##STR184## R₄ is hydrogen and R₅ is hydrogen or4-halo.
 32. A compound according to claim 31 in which R₅ is hydrogen.33. A compound according to claim 31 in which R₅ is 4-chloro.
 34. Acompound according to claim 31 in which R₅ is 4-fluoro.
 35. A compoundaccording to claim 3 in which R₃ is ##STR185##
 36. A compound accordingto claim 35 in which R₃ is ##STR186##
 37. A compound according to claim36 in which R₃ is ##STR187##
 38. A compound according to claim 37 inwhich R₃ is ##STR188##
 39. A compound according to claim 38 in which R₄is hydrogen.
 40. A compound according to claim 38 in which R₅ ishydrogen.
 41. A compound according to claim 38 in which R₄ and R₅ areboth hydrogen.
 42. A compound according to claim 38 in which R₄ and R₅are both monohalo.
 43. A compound according to claim 42 in which R₄ andR₅ are both 4-fluoro.
 44. A compound according to claim 42 in which R₄is 4-fluoro and R₅ is 4-chloro.
 45. A compound according to claim 38 inwhich R₄ is 4-fluoro and R₅ is difluoro.
 46. A compound according toclaim 37 in which R₃ is ##STR189## R₄ is hydrogen and R₅ is hydrogen or4-halo.
 47. A compound according to claim 38 in which R₄, R₅ and R₁₃ areall hydrogen.
 48. A compound according to claim 38 in which R₄, R₅, R₁₂and R₁₃ are all hydrogen.
 49. A compound according to claim 38 in whichR₄ is 4-halo and R₅ and R₁₃ are both hydrogen.
 50. A compound accordingto claim 49 in which R₄ is 4-fluoro.
 51. A compound according to claim38 in which R₅ is 4-halo and R₄ and R₁₃ are both hydrogen.
 52. Acompound according to claim 51 in which R₅ is 4-fluoro.
 53. A compoundaccording to claim 51 in which R₅ is 4-chloro.
 54. A compound accordingto claim 38 in which R₄ and R₅ are both 4-halo and R₁₃ is hydrogen. 55.A compound according to claim 54 in which R₄ and R₅ are both 4-fluoro.56. A compound according to claim 54 in which R₄ is 4-fluoro and R₅ is4-chloro.
 57. A compound according to claim 38 in which R₁₁ is chloro,R₁₂ is fluoro, and R₁₃ is hydrogen.
 58. A compound according to claim 37in which R₃ is ##STR190## R₄ is hydrogen and R₅ is hydrogen or 4-halo.59. A compound according to claim 58 in which R₅ is hydrogen.
 60. Acompound according to claim 58 in which R₅ is 4-chloro.
 61. A compoundaccording to claim 58 in which R₅ is 4-fluoro.
 62. A compound accordingto claim 58 in which R₁₁ is chloro, R₁₂ is fluoro and R₁₃ is hydrogen.63. A compound according to claim 19 in which R₃ is ##STR191##
 64. Acompound according to claim 19 in which R₃ is ##STR192##
 65. A compoundaccording to claim 1 in which R₃ is ##STR193## and R₉ is 4-propargyl.66. A compound according to claim 65 in which R₁ is 3- or4-trifluoromethylphenyl.
 67. A compound according to claim 1 in which R₁is 3-chlorophenyl, R₂ is dichloromethyl and R₃ is 3-phenoxybenzyl.
 68. Acompound according to claim 1 in which R₁ is 4-chlorophenyl, R₂ isisopropyl and R₃ is 3-phenoxybenzyl.
 69. A compound according to claim 1in which R₁ is 3-chlorophenyl, R₂ is isopropyl and R₃ is3-phenoxybenzyl.
 70. A compound according to claim 1 in which R₁ is3,4-dichlorophenyl, R₂ is isopropyl and R₃ is 3-phenoxybenzyl.
 71. Acompound according to claim 1 in which R₁ is 4-chlorophenyl, R₂ isisopropyl and R₃ is 3-phenoxy,4-fluorobenzyl.
 72. A compound accordingto claim 1 in which R₁ is 3,4-dichlorophenyl, R₂ is isopropyl and R₃ is3-(4-fluorophenoxy)benzyl.
 73. A compound according to claim 1 in whichR₁ is pentafluorophenyl, R₂ is isopropyl and R₃ is 3-phenoxybenzyl. 74.A compound according to claim 1 in which R₁ is 3,4-difluorophenyl, R₂ isisopropyl and R₃ is 3-phenoxybenzyl.
 75. A compound according to claim 1in which R₁ is 3-trifluoromethylphenyl, R₂ is isopropyl and R₃ is3-phenoxybenzyl.
 76. A compound according to claim 1 in which R₁ is3-trifluoromethyl,4-fluorophenyl, R₂ is isopropyl and R₃ is3-phenoxybenzyl.
 77. A compound according to claim 1 in which R₁ is3-trifluoromethylphenyl, R₂ is isopropyl and R₃ is3-phenoxy,4-fluorobenzyl.
 78. A compound according to claim 1 in whichR₁ is 3-chloro,4-fluorophenyl, R₂ is isopropyl and R₃ is3-phenoxybenzyl.
 79. A compound according to claim 1 in which R₁ is3-chloro,4-fluorophenyl, R₂ is isopropyl and R₃ is3-phenoxy,4-fluorobenzyl.
 80. A compound according to claim 1 in whichR₁ is 3-chloro,4-fluorophenyl, R₂ is isopropyl and R₃ is3-(4-fluorophenoxy)benzyl.
 81. A compound according to claim 1 in whichR₁ is 3-chloro,4-fluorophenyl, R₂ is ethyl and R₃ is3-(4-fluorophenoxy)benzyl.
 82. A compound according to claim 1 in whichR₁ is 3-chloro,4-fluorophenyl, R₂ is isopropyl and R₃ is6-(4-fluorophenoxy)-pyrid-2-ylmethyl.
 83. A compound according to claim1 in which R₁ is 3-chloro,4-fluorophenyl, R₂ is isopropyl and R₃ is6-(4-chlorophenoxy)-pyrid-2-ylmethyl.
 84. A compound according to claim1 in which R₁ is 3-chloro,4-fluorophenyl, R₂ is secondary butyl and R₃is 3-phenoxybenzyl.
 85. A compound according to claim 1 in which R₁ is4-isopropylphenyl, R₂ is isopropyl and R₃ is 3-phenoxybenzyl.
 86. Acompound according to claim 1 in which R₁ is 4-(tertiary butyl)phenyl,R₂ is isopropyl and R₃ is 3-phenoxybenzyl.
 87. A compound according toclaim 1 in which R₁ is 4-ethylphenyl, R₂ is tertiary butyl and R₃ is3-phenoxybenzyl.
 88. A compound according to claim 1 in which R₁ is3,4-methylenedioxyphenyl, R₂ is isopropyl and R₃ is 3-phenoxybenzyl. 89.A compound according to claim 1 in which R₁ is 3,4-methylenedioxyphenyl,R₂ is secondary butyl and R₃ is 3-phenoxybenzyl.
 90. A compoundaccording to claim 1 in which R₁ is 4-chlorophenyl, R₂ is isopropyl andR₃ is 3-(4-fluorophenoxy)benzyl.
 91. A compound according to claim 1 inwhich R₁ is 3-chlorophenyl, R₂ is isopropyl and R₃ is3-(4-fluorophenoxy)benzyl.
 92. A compound according to claim 1 in whichR₁ is 3-trifluoromethylphenyl, R₂ is isopropyl and R₃ is3-(4-fluorophenoxy)benzyl.
 93. A compound according to claim 1 in whichR₁ is 3-chloro,4-fluorophenyl, R₂ is isopropyl and R₃ is3-(4-fluorophenoxy),4-fluorobenzyl.
 94. A compound according to claim 1in which R₁ is 3-chloro,4-fluorophenyl, R₂ is isopropyl and R₃ is3-(3,4-difluorophenoxy)benzyl.
 95. A compound according to claim 1 inwhich R₁ is 3-chloro,4-fluorophenyl, R₂ is isopropyl and R₃ is3-(4-bromophenoxy)benzyl.
 96. A compound according to claim 1 in whichR₁ is 3-chloro,4-fluorophenyl, R₂ is isopropyl and R₃ is3-(4-chlorophenoxy)benzyl.
 97. A compound according to claim 1 in whichR₁ is 5-(2,2-dimethyl-1,3-benzodioxolyl), R₂ is isopropyl and R₃ is3-phenoxy,4-fluorobenzyl.
 98. A compound according to claim 1 in whichR₁ is 3,4-(difluoromethylenedioxy)phenyl, R₂ is isopropyl and R₃ is3-(4-fluorophenoxy)benzyl.
 99. A compound according to claim 1 in whichR₁ is 3-iodophenyl, R₂ is isopropyl and R₃ is 3-(4-fluorophenoxy)benzyl.100. A compound according to claim 1 in which R₁ is3-chloro-4-trifluoromethoxyphenyl, R₂ is isopropyl and R₃ is3-(4-fluorophenoxy),4-fluorobenzyl.
 101. A compound according to claim 1in which R₁ is 3-trifluoromethylphenyl, R₂ is isopropyl and R₃ is2,3,5,6-tetrafluoro-4-propargylbenzyl.
 102. A compound according toclaim 1 in which R₁ is 4-trifluoromethylphenyl, R₂ is isopropyl, and R₃is 2,3,5,6-tetrafluoro-4-propargylbenzyl.
 103. A method for controllinginsects comprising applying to an insect, the locus of an insect or alocus at which insecticidal control is desired, an insecticidallyeffective amount of a compound according to claim
 1. 104. A method forcontrolling insects according to claim 103 in which the insect is amember of the order Lepidoptera.
 105. A method for controlling insectsaccording to claim 103 in which the insect is a member of the otherColeoptera.
 106. A method for controlling insects according to claim 103in which the insect is a member of the order Hemiptera.
 107. A methodfor controlling insects comprising applying to an insect, the locus ofan insect, or a locus at which insecticidal control is desired, aninsecticidally effective amount of a compound according to claim
 3. 108.A method for controlling insects comprising applying to an insect, thelocus of an insect or a locus at which insecticidal control is desired,an insecticidally effective amount of a compound according to claim 8.109. A method for controlling insects comprising applying to an insect,the locus of an insect or a locus at which insecticidal control isdesired, an insecticidally effective amount of a compound according toclaim
 23. 110. A method for controlling insects comprising applying toan insect, the locus of an insect or a locus at which insecticidalcontrol is desired, an insecticidally effective amount of a compoundaccording to claim
 38. 111. An insecticidal composition comprising:(a)an insecticidally effective amount of a compound according to claim 1;and (b) an insecticidally suitable diluent or carrier.
 112. A compoundaccording to claim 1 in which R₁ is ##STR194## wherein R₁₁ is hydrogen,halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄haloalkoxy, C₁ -C₄ alkylthio, C₁ -C₄ haloalkylthio, C₂ -C₅ carboalkoxy,C₂ -C₅ alkylcarbonyl, nitro or cyano; R₁₂ is hydrogen, halogen, C₁ -C₄alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄alkylthio; nitro, cyano, C₁ -C₄ alkylsulfonyl, C₂ -C₅ alkylcarbonyl orC₂ -C₅ carboalkoxy; and R₁₃ is hydrogen, halogen, C₁ -C₄ haloalkyl or C₁-C₄ alkoxy, or R₁₁ and R₁₂ taken together are C₂ -C₄ alkylene, C₂ -C₄alkyleneoxy, C₁ -C₄ alkylenedioxy or halo-C₁ -C₃ alkylenedioxy.
 113. Acompound according to claim 112 in which R₁₃ is hydrogen and R₁₁ and R₁₂are other than hydrogen.
 114. A compound according to claim 112 in whichR₁₁ and R₁₃ are hydrogen.
 115. A compound according to claim 112 inwhich R₁₂ and R₁₃ are hydrogen.
 116. A compound according to claim 112in which R₁₂ is a C₁ -C₂ polyhaloalkoxy group containing at least onefluorine atom and R₁₃ is hydrogen or halogen.
 117. A compound accordingto claim 116 in which R₁₁ is halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁-C₄ alkoxy or C₁ -C₄ haloalkoxy; and R₁₃ is hydrogen.
 118. A compoundaccording to claim 112 in which R₁₁ and R₁₂ are both halogen, and R₁₃ ishydrogen.
 119. A compound according to claim 117 in which R₂ is ethyl,isopropyl, isopropenyl or dichloromethyl.
 120. A compound according toclaim 112 in which R₁₁ is halogen; R₁₂ is trifluoromethoxy; and R₁₃ ishydrogen.
 121. A compound according to claim 112 in which R₃ is##STR195##
 122. A compound according to claim 121 in which R₃ is##STR196##
 123. A compound according to claim 122 in which R₄ ishydrogen.
 124. A compound according to claim 122 in which R₅ ishydrogen.
 125. A compound according to claim 122 in which R₄ and R₅ areboth hydrogen.
 126. A compound according to claim 122 in which R₄ and R₅are both mono-halo.
 127. A compound according to claim 122 in which R₄and R₅ are both 4-fluoro.
 128. A compound according to claim 122 inwhich R₄ is 4-fluoro and R₅ is 4-chloro.
 129. A compound according toclaim 121 in which R₃ is ##STR197## R₄ is hydrogen; and R₅ is hydrogenor 4-halo.
 130. A compound according to claim 1 in which R₁ is3-fluoro-4-trifluoromethoxyphenyl; R₂ is isopropyl; and R₃ is3-(4-fluorophenoxy),4-fluorobenzyl.
 131. A method for controllinginsects comprising applying to an insect, the locus of an insect, or alocus in which insecticidal control is desired, an insecticidallyeffective amount of a compound according to claim
 112. 132. A method forcontrolling insects comprising applying to an insect, the locus of aninsect, or a locus in which insecticidal control is desired, aninsecticidally effective amount of a compound according to claim 121.133. An insecticidal composition comprising: (a) an insecticidallyeffective amount of a compound according to claim 112; and (b) aninsecticidally suitable diluent or powder.
 134. A compound according toclaim 1 in which R₁ is 3,4-dichlorophenyl; R₂ is isopropyl; and R₃ is3-(4-fluorophenoxy)-4-fluorobenzyl.